Benzyl Chloride → HCID 178462733, compound

HRID 1633750Notes

Reaction equation

HRID 1633750 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1[CH:14]=[N+:13]([C@@H:15]2[O:19][C@H:18]([CH2:20][O:21][P:22]([O:25][P:26]([O:29][CH2:30][C@H:31]3[O:35][C@@H:34]([N:36]4[C:40]5[N:41]=[CH:42][N:43]=[C:44]([NH2:45])[C:39]=5[N:38]=[CH:37]4)[C@H:33]([OH:46])[C@@H:32]3[OH:47])([OH:28])=[O:27])([O-:24])=[O:23])[C@@H:17]([OH:48])[C@H:16]2[OH:49])[CH:12]=[C:11]([C:50]([NH2:52])=[O:51])[CH:10]=1.[CH:53]([C:55]1[NH:56][CH:57]=[CH:58][N:59]=1)=[CH2:54].[CH2:60]([Cl:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C=O)C>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1[CH:14]=[N+:13]([C@@H:15]2[O:19][C@H:18]([CH2:20][O:21][P:22]([O:25][P:26]([O:29][CH2:30][C@H:31]3[O:35][C@@H:34]([N:36]4[C:40]5[N:41]=[CH:42][N:43]=[C:44]([NH2:45])[C:39]=5[N:38]=[CH:37]4)[C@H:33]([OH:46])[C@@H:32]3[OH:47])([OH:28])=[O:27])([O-:24])=[O:23])[C@@H:17]([OH:48])[C@H:16]2[OH:49])[CH:12]=[C:11]([C:50]([NH2:52])=[O:51])[CH:10]=1.[CH:53]([C:55]1[NH:56][CH:57]=[CH:58][N:59]=1)=[CH2:54].[CH:9]1[CH:14]=[N+:13]([C@@H:15]2[O:19][C@H:18]([CH2:20][O:21][P:22]([O:25][P:26]([O:29][CH2:30][C@H:31]3[O:35][C@@H:34]([N:36]4[C:40]5[N:41]=[CH:42][N:43]=[C:44]([NH2:45])[C:39]=5[N:38]=[CH:37]4)[C@H:33]([OH:46])[C@@H:32]3[OH:47])([OH:28])=[O:27])([O-:24])=[O:23])[C@@H:17]([OH:48])[C@H:16]2[OH:49])[CH:12]=[C:11]([C:50]([NH2:52])=[O:51])[CH:10]=1.[Cl-:67].[CH:34]([N+:36]1[CH:40]=[CH:39][N:38]([CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:37]=1)=[CH2:33]

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 131723641HCID 131723641, compound

Product 1

HCID 178462733HCID 178462733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Next, to a 1-L 3-necked round-bottomed flask equipped with a mechanical stirrer and a reflux condenser was added 625 g of the 20.0 wt. % solution of styrene-co-1-vinylimidazole in DMF. Benzyl chloride (8.0 g) was added, and the solution was stirred and heated at 100° C. under a slight positive pressure of nitrogen for 18 hr. A portion of the solution (25 g) was removed for analysis. Then, 9.7 g of 2-chloroethanol was added, and the solution was reheated with stirring at 100° C. for an additional 18 hr. The reaction mixture was cooled and the polymer was precipitated into diethyl ether with rapid stirring. The flaky precipitate was washed well with diethyl ether and dried in a vacuum oven.

Workup

  1. customNext, to a 1-L 3-necked round-bottomed flask equipped with a mechanical stirrer and a reflux condenser
  2. customA portion of the solution (25 g) was removed for analysis
  3. additionThen, 9.7 g of 2-chloroethanol was added
  4. stirringwith stirring at 100° C. for an additional 18 hr
  5. temperatureThe reaction mixture was cooled
  6. customthe polymer was precipitated into diethyl ether with rapid stirring
  7. washThe flaky precipitate was washed well with diethyl ether
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-430d49586eb249fc9e100a505b471ec3
Source dataset
uspto-grants-2003_01
Patent number
US06503607B1

Reaction notes

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