1-Acetoxy-2-bromoethane → HCID 14372575, compound

HRID 620278Notes

Reaction equation

HRID 620278 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([OH:19])[CH:3]=1.Br[CH2:21][CH2:22][O:23][C:24](=[O:26])[CH3:25]>C(#N)C>[C:24]([O:23][CH2:22][CH2:21][O:19][C:4]1[CH:3]=[C:2]([NH2:1])[C:17]([Cl:18])=[CH:16][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 14372575HCID 14372575, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the tetrabutylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (5.27 g, 10 mmoles) (prepared in Preparation No. 3) in acetonitrile (100 ml) and 2-bromoethylacetate (2 g, 12 mmoles) was stirred for 48 hours. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic layer was washed with ice-cold 0.4N sodium hydroxide solution, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100 ), methanol (2), ammonia (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated to leave a residue of 3.18 g (85%) of the title compound. Crystallization from toluene gave a sample, mp. 101°-102° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with ice-cold 0.4N sodium hydroxide solution, water
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was chromatographed over deactivated silica
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-eec40a5104f54b0dbe9ac58825ade751
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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