Thionyl Chloride → 6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid

HRID 268035Notes

Reaction equation

HRID 268035 reaction equation
S(Cl)(Cl)=O.C([O:7][C:8](=[O:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([OH:26])=O)=[CH:12][CH:11]=1)C>>[O:26]=[C:24]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][S:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][C:8]([OH:7])=[O:27])=[CH:11][C:12]1=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 544601824-(2-Carboxybenzyl-thio)phenyl-acetic acid ethyl ester

Product 1

HCID 123300366,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid

Procedure

66 cc of thionyl chloride are added at room temperature to 13.2 g of 4-(2-carboxy-benzyl-thio)phenyl-acetic acid ethyl ester and the mixture is stirred for 90 minutes until gas evolution stops. The mixture is completely concentrated by evaporation at reduced pressure and the resulting light yellow oil is dissolved in ether, whereby 4-(2-chloro-carbonyl-benzyl-thio)phenyl-acetic acid ethyl ester precipitates in the form of light yellow crystals. M.P. 78°-79°.

Workup

  1. concentrationThe mixture is completely concentrated by evaporation at reduced pressure
  2. dissolutionthe resulting light yellow oil is dissolved in ether
  3. customwhereby 4-(2-chloro-carbonyl-benzyl-thio)phenyl-acetic acid ethyl ester precipitates in the form of light yellow crystals

Sources & evidence

ORD record
ord-4bca375f8778470eb36b792f4ddae386
Source dataset
uspto-grants-1976_03
Patent number
US03946036

Reaction notes

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