2-Bromo-1-(3-nitrophenyl)ethan-1-one → HCID 804928, compound

HRID 581947Notes

Reaction equation

HRID 581947 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]([NH2:17])(=[S:16])[CH3:15]>C(O)(=O)C>[CH3:15][C:14]1[S:16][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[N:17]=1

Participants

4

Reactant 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 2723949Thioacetamide

Product 1

HCID 804928HCID 804928, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-3'-nitroacetophenone (5 g, 20.5 mmol) and thioacetamide (1.4 g, 18.6 mmol). in glacial acetic acid (50 ml) is heated to reflux over night. After cooling the precipitate is filtered off, washed with water and dried to yield 2-methyl-4-(3-nitrophenyl)thiazole (3.47 g, 85%). Mp 87-88° C. This product is hydrogenated as described in Example 4 to yield 2n quantitatively. Mp 80-81° C.

Workup

  1. temperatureto reflux over night
  2. temperatureAfter cooling the precipitate
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4bac0097d452449ca8f063508493bd7f
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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