2,2-Dimethoxyethylmethylamine → ethyl 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene-2-carboxylate

HRID 1084684Notes

Reaction equation

HRID 1084684 reaction equation
Br[CH2:2][C:3]1[C:4]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:5]=2[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:18][O:19][CH:20]([O:24][CH3:25])[CH2:21][NH:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:17][C:15]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:3]([CH2:2][N:22]([CH2:21][CH:20]([O:24][CH3:25])[O:19][CH3:18])[CH3:23])[C:4]=2[CH:16]=1

Participants

5

Reactant 3

HCID 85032,2-DimethoxyethylmethylamineHCID 11430Potassium CarbonateHCID 14836261Ethyl 3-Bromomethyl-5-chlorobenzo[b]thiophene-2-carboxylate

Product 1

HCID 14836262ethyl 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene-2-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 3-bromomethyl-5-chlorobenzo[b]thiophene-2-carboxylate (11.0 g, 0.033 mol), methylaminoacetaldehyde dimethyl acetal (4.76 g, 0.04 mol) and potassium carbonate (11.4 g, 0.8 mol) in dry acetone (200 ml) was stirred for 48 hours, filtered and the filtrate concentrated to give 11.8 g (96%) of ethyl 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl-(aminomethyl)]benzo[b]thiophene-2-carboxylate.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c366e179d6e44e2cb63c100477acddd3
Source dataset
uspto-grants-1991_04
Patent number
US05006521

Reaction notes

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