3-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acid → HCID 131711831, compound

HRID 2058040Notes

Reaction equation

HRID 2058040 reaction equation
[Br:1][CH:2]([C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5].[SH:16][C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=1>C(O)(=O)C>[BrH:1].[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([CH:2]([S:16][C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[CH2:3][C:4]([OH:6])=[O:5])=[O:15])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 1696663-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acidHCID 178480602HCID 178480602, compound

Product 1

HCID 131711831HCID 131711831, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-bromo-3-(p-chlorobenzoyl)propionic acid (11.64 g., 0.04 m.) and 2-mercapto-1-methylimidazole (4.56 g., 0.04 m.) is dissolved in glacial acetic acid by warming on a steam bath. After filtration of a small amount of insoluble material the filtrate is evaporated. The residue is washed with ether and then treated with dimethoxyethane and the solid weighing 10 g. is collected. The crude material is recrystallized from acetonitrile. The pure compound melts at 173°-5°.

Workup

  1. temperatureby warming on a steam bath
  2. filtrationAfter filtration of a small amount of insoluble material the filtrate
  3. customis evaporated
  4. washThe residue is washed with ether
  5. additiontreated with dimethoxyethane
  6. customis collected
  7. customThe crude material is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-81b86ab91f314a61a3821b13a06a745f
Source dataset
uspto-grants-1980_07
Patent number
US04214089

Reaction notes

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