1-Chloro-4-(chloromethyl)benzene → 1-[(4-Chlorophenyl)methyl]-2-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid

HRID 484262Notes

Reaction equation

HRID 484262 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[S:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH:13]=2)[NH:8][C:7]=1[CH3:26])C.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>CO>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH2:16][C:17]4[S:18][C:19]5[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=5[N:21]=4)=[CH:11][CH:10]=3)[C:6]([CH2:5][C:4]([OH:3])=[O:27])=[C:7]2[CH3:26])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 152880242-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid ethyl ester

Product 1

HCID 152880251-[(4-Chlorophenyl)methyl]-2-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is prepared according to the method of Example 16 using 2-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid ethyl ester and 4-chlorobenzyl chloride; however, the hydrolysis is carried out in aqueous methanol. Recrystallization from acetonitrile affords white crystals, m.p. 175°-176° C.

Workup

  1. customRecrystallization from acetonitrile
  2. customaffords white crystals, m.p. 175°-176° C.

Sources & evidence

ORD record
ord-74dc7494cc524bb69f76f24cbcd8a3d2
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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