<!--

       Copyright 2011 Peter Murray-Rust et. al.

       Licensed under the Apache License, Version 2.0 (the "License");
       you may not use this file except in compliance with the License.
       You may obtain a copy of the License at

           http://www.apache.org/licenses/LICENSE-2.0

       Unless required by applicable law or agreed to in writing, software
       distributed under the License is distributed on an "AS IS" BASIS,
       WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
       See the License for the specific language governing permissions and
       limitations under the License.

-->

<cml xmlns="http://www.xml-cml.org/schema">
  <moleculeList>
    <molecule id="m1" title="2-phenyl-2-[(2,2,6,6-tetramethylpiperidino)oxyl]-1-ethanol">
      <formula concise="C 17 H 27 N 1 O 2"/>
    </molecule>
    <molecule id="m2" title="triethylamine">
      <formula concise="C 6 H 15 N 1"/>
      <property name="density">
        <scalar dataType="xsd:float" dictRef="cml:density" units="units:g.cm-3">0.728</scalar>
      </property>
    </molecule>
    <molecule id="m3" title="2-bromopropanoyl bromide">
      <formula concise="C 3 H 4 Br 2 O 1"/>
      <property name="density">
        <scalar dataType="xsd:float" dictRef="cml:density" units="units:g.cm-3">2.061</scalar>
      </property>
    </molecule>
    <molecule id="2a" title="2-phenyl-2-[(2,2,6,6-tetramethylpiperidino)oxy]ethyl 2-bromo propanoate">
      <formula concise="C 20 H 30 N 1 O 2 Br 1"/>
    </molecule>
    <molecule id="m4" title="triethylammonium">
      <formula concise="C 6 H 16 N 1 1"/>
    </molecule>
    <molecule id="m5" title="bromide">
      <formula concise="Br 1 -1"/>
    </molecule>
  </moleculeList>

  <substanceList>
    <substance id="ss1" role="cml:solvent">
      <molecule id="s1" ref="thf"/>
    </substance>
  </substanceList>
      
  <reactionScheme title="Synthesis of Asymmetric initiators" id="2.2">
    <reaction title="Synthesis of 2a" id="rc1">
      <reactantList>
        <reactant id="r1" count="1" title="2-phenyl-2-1-ethanol">
          <molecule ref="m1"/>
          <amount id="a1" units="units:g" unitType="unitType:mass">0.85</amount>
          <amount id="a1m" units="units:mmol">3.06</amount>
        </reactant>
        <reactant id="r2" count="1" title="ET3N">
          <molecule ref="m2"/>
          <amount id="a2" units="units:ml">0.7</amount>
          <amount id="a2m" units="units:mmol">5</amount>
        </reactant>
        <reactant id="r3" count="1" title="2-bromo propanyol bromide">
          <molecule ref="m3"/>
          <amount id="a3" units="units:ml">0.53</amount>
          <amount id="a3m" units="units:mmol">5</amount>
        </reactant>
      </reactantList>
      
      <productList>
        <product id="p1" count="1" title="2a" color="pale yellow" state="oil">
          <molecule ref="2a"/>
          <amount id="a5" units="units:g">0.52</amount>
          <amount id="a6" units="units:percent">41</amount>
        </product>
        <product id="p2">
          <molecule ref="m4"/>
        </product>
        <product id="p3">
          <molecule ref="m5"/>
        </product>
      </productList>
    </reaction>
  </reactionScheme>
    
  <actionList>
    <action role="reaction">
      <reaction ref="rc1"/>
      <conditionList>
        <scalar id="sc1" dictRef="cml:method">stirred</scalar>
        <scalar id="sc2" dictRef="cml:temp" units="units:celsius">0</scalar>
        <scalar id="sc3" dictRef="cml:atmosphere">nitrogen</scalar>
        <scalar id="sc4" dictRef="cml:duration" units="units:hour">1</scalar>
      </conditionList>
      <object role="cml:container">round-bottom-flask</object>
      <action role="add">
        <reactant ref="r1"/>
      </action>
      <action role="add">
        <reactant ref="r2"/>
      </action>
      <action role="add">
        <substance ref="s1" role="solvent">
          <amount id="a4" units="units:ml">20</amount>
        </substance>
      </action>
      <action role="add" duration="1 hour">
        <scalar dictRef="cml:dropwise"/>
        <reactant ref="r3"/>
        <substance ref="s1" role="solvent">
          <amount id="a4" units="units:ml">20</amount>
        </substance>
      </action>
      <conditionList>
        <scalar id="sc5" dictRef="cml:temp" units="units:celsius">21</scalar>
        <scalar id="sc6" dictRef="cml:duration">overnight</scalar>
      </conditionList>
    </action>
    
    <actionList role="workup">
      <action role="filtration"/>
      <action role="solventEvaporation"/>
      <action role="redissolve">
        <substance id="ss2" role="cml:solvent">
          <molecule id="m5" ref="CH2Cl2"/>
        </substance>
      </action>
      
      <action role="neutralize">
        <substance id="ss3" role="cml:base">
          <molecule id="m6" ref="Na2CO3"/>
        </substance>
      </action>
      
      <action role="dry">
        <substance id="ss4" role="cml:drier">
          <molecule id="m7" ref="Na2SO4"/>
        </substance>
      </action>
      
      <action role="purification">
        <substanceList role="cml:solvent">
          <substance id="ss5">
            <molecule id="m8" ref="hexane"/>
            <amount id="a5" unitType="unitType:vol">8</amount>
          </substance>
          <substance id="ss6">
            <molecule id="m9" ref="ethyl"/>
            <amount id="a6" unitType="unitType:vol">2</amount>
          </substance>
        </substanceList>
      </action>
      
    </actionList>
    
  </actionList>
  
</cml>
