Phenacyl bromide → HCID 13476634, compound

HRID 1285384Notes

Reaction equation

HRID 1285384 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([CH3:12])[C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:15][C:13]([C:7]1[S:6][C:5]2[N:4]([C:1](=[O:3])[CH3:2])[C:19]([C:20](=[O:21])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:10]([NH2:11])[C:9]=2[C:8]=1[CH3:12])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 90296Ethyl 5-acetamido-4-cyano-3-methylthenoate

Product 1

HCID 13476634HCID 13476634, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

250 g of 2-acetamido-3-cyano-4-methyl-5-ethoxycarbonylthiophene, prepared in accordance with the method of K. Gewald, are refluxed for 24 hours in 1500 ml of acetone with 250 g of α-bromoacetophenone and 220 g of potassium carbonate; the whole is then precipitated in 4000 ml of ice-water. The resulting precipitate is filtered, washed with 1000 ml of an iced mixture of water/ethanol (1/1), then dried and finally washed with 1000 ml of a cold mixture of cyclohexane/benzene (9/1). In this manner 295 g of 2-ethoxycarbonyl-3-methyl-4-amino-5-benzoyl-6-acetylthieno[2,3-b]pyrrole are obtained, m.p.: 188° C.

Workup

  1. customthe whole is then precipitated in 4000 ml of ice-water
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with 1000 ml of an iced mixture of water/ethanol (1/1)
  4. customdried
  5. washfinally washed with 1000 ml of a cold mixture of cyclohexane/benzene (9/1)

Sources & evidence

ORD record
ord-8777bd1be36243eca06368f1293ef212
Source dataset
uspto-grants-1986_01
Patent number
US04567196

Reaction notes

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