Phenacyl bromide → (3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amine

HRID 130350

Reaction equation

HRID 130350 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 710776N-(3,4-Dichlorophenyl)thiourea

Product 1

HCID 86228547(3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (3,4-Dichloro-phenyl)-thiourea (2 g, 9.04 mmol) in ethanol (35 mL) was added 2-Bromo-1-phenyl-ethanone and the solution was refluxed overnight. The reaction mixture was allowed to cool to room temperature and the resulting solid was filtered and washed with cold ethyl acetate to yield 2.45 g (85%) of an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.16 (d, J=1.8 Hz, 1H), 7.87 (d, J=7.5 Hz, 2 H), 7.61-7.29 (m, 6H); LCMS m/z 319 [M−1]

Workup

  1. temperaturethe solution was refluxed overnight
  2. filtrationthe resulting solid was filtered
  3. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-8a202ee4d2fb468b8ed0a91ab4595007
Source dataset
uspto-grants-2008_06
Patent number
US07381736B2

Linked notes

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