2-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one → HCID 13151131, compound

HRID 848766Notes

Reaction equation

HRID 848766 reaction equation
[C:1]([NH:4][C:5]([N:7]([CH3:9])[CH3:8])=[S:6])(=O)[CH3:2].[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([C:15](=[O:18])[CH2:16]Br)=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>C(O)(C)C>[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([C:16]2[S:6][C:5]([N:7]([CH3:9])[CH3:8])=[N:4][C:1]=2[CH3:2])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-oneHCID 13134167HCID 13134167, compound

Product 1

HCID 13151131HCID 13151131, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The starting material is prepared as follows: A mixture of 3.7 g of N-acetyl-N',N'-dimethyl-thiourea and 7 g of 4-chloro-3-nitro-phenacyl bromide in 100 ml of isopropanol is refluxed for 2 hours, cooled and filtered. The residue is rendered basic and extracted with methylene chloride. The extract is dried and evaporated and the residue is recrystallised from a mixture of ethyl acetate and hexane, yielding 4-chloro-3-nitro-1-(4-methyl-2-dimethylamino-5-thiazoloyl)-benzene, which melts at 165°-169°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. extractionextracted with methylene chloride
  6. customThe extract is dried
  7. customevaporated
  8. customthe residue is recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a354118cb09546babbb1b35628b7af3f
Source dataset
uspto-grants-1981_10
Patent number
US04297365

Reaction notes

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