2,2-Dimethoxyethylmethylamine → HCID 14836262, compound

HRID 703065Notes

Reaction equation

HRID 703065 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 14836262HCID 14836262, compoundYield 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-c773b5d80deb4282b1b5e0339433151b
Source dataset
uspto-grants-1991_01
Patent number
US04981848

Reaction notes

Loading…