2,2-Dimethoxyethylmethylamine → ethyl 5-chloro-3-[N-(2,2 dimethoxyethyl)-N methyl(aminomethyl)]-2-benzofurancarboxylate

HRID 703060Notes

Reaction equation

HRID 703060 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[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:12][C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:3]([CH2:2][N:22]([CH2:21][CH:20]([O:24][CH3:25])[O:19][CH3:18])[CH3:23])[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 85032,2-DimethoxyethylmethylamineHCID 11430Potassium CarbonateHCID 15678689Ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylate

Product 1

HCID 15678690ethyl 5-chloro-3-[N-(2,2 dimethoxyethyl)-N methyl(aminomethyl)]-2-benzofurancarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylate (52.75 g, 0.166 mol), methylaminoacetaldehyde dimethyl acetal (19.0 g, 0.167 mol) and potassium carbonate (45 g) in dry acetone (600 ml) was stirred under argon for 30 hours, filtered and the filtrate evaporated. The residue was partitioned between ethyl ether and water and the organic phase was dried with magnesium sulfate, filtered, and concentrated to give ethyl 5-chloro-3-[N-(2,2 dimethoxyethyl)-N methyl(aminomethyl)]-2 -benzofurancarboxylate: mp 58°-60° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between ethyl ether and water
  4. dry with materialthe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7987011e08d479b935addacc6d74603
Source dataset
uspto-grants-1991_01
Patent number
US04981849

Reaction notes

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