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

HRID 1111102Notes

Reaction equation

HRID 1111102 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-8d38d819b1f043fca57ceec45a2a035a
Source dataset
uspto-grants-1990_12
Patent number
US04978660

Reaction notes

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