Phenacyl bromide → N~1~-(4-Phenyl-1,3-thiazol-2-yl)benzene-1,3-diamine

HRID 2086775Notes

Reaction equation

HRID 2086775 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH2:14])=[S:13])[CH:8]=[CH:9][CH:10]=1)(=O)C.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(O)C>[C:19]1([C:17]2[N:14]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[NH2:4])[S:13][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 6451295Acetamide, N-(3-((aminothioxomethyl)amino)phenyl)-

Product 1

HCID 22724394N~1~-(4-Phenyl-1,3-thiazol-2-yl)benzene-1,3-diamineYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(3-acetylaminophenyl)thiourea (0.84 g) and 2-bromoacetophenone (0.84 g) in ethanol (10 ml) was refluxed for 15 minutes. After evaporation of the solvent, 3N hydrochloric acid was added thereto and the mixture was refluxed for 30 minutes. The mixture was made basic with sodium bicarbonate and extracted with ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 3-(4-phenylthiazol-2-yl)aminoaniline (0.88 g).

Workup

  1. temperaturewas refluxed for 15 minutes
  2. customAfter evaporation of the solvent, 3N hydrochloric acid
  3. additionwas added
  4. temperaturethe mixture was refluxed for 30 minutes
  5. extractionextracted with ethyl acetate
  6. washThe organic solution was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-6cd90584d27645e1bf2ef90a9cd72202
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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