5-[(2-Chlorophenyl)carbonyl]-1,3-thiazol-2-amine → Ethanone, 1-(2-chlorophenyl)-

HRID 45270

Reaction equation

HRID 45270 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[O:8])=[CH:5][N:6]=1.[Cl:16][C:17]1[CH:34]=[CH:33][CH:32]=[CH:31][C:18]=1[C:19]([C:21]1SC(N=CN(C)C)=NC=1)=[O:20]>Cl>[NH2:1][C:2]1[S:3][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[O:8])=[CH:5][N:6]=1.[Cl:16][C:17]1[CH:34]=[CH:33][CH:32]=[CH:31][C:18]=1[C:19](=[O:20])[CH3:21]

Participants

5

Reactant 2

HCID 574569435-[(2-Chlorophenyl)carbonyl]-1,3-thiazol-2-amineHCID 66628633N'-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine

Product 2

HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 574569435-[(2-Chlorophenyl)carbonyl]-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

(2-Amino-thiazol-5-yl)-(2-chloro-phenyl)-methanone The crude N′-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine was dissolved in 10% hydrochloric acid (150 mL) and heated at 70° C. for 4 hours. The precipitate was filtered, washed with ether, and then suspended in a 10% sodium carbonate solution (250 mL). The suspension was stirred for 1 hour and the precipitate was filtered, washed with ether, and dried in air to give (2-amino-thiazol-5-yl)-(2-chloro-phenyl)-methanone as a brown solid (8.5 g, 36 mmol, 55% from 1-(2-chloro-phenyl)-ethanone). ESI-MS m/z calc. 238.0. found 239.3 (M+1)+1; 1H NMR (DMSO) δ 7.25 (s, 1H), 7.42-7.55 (m, 4H), 8.35 (s, 2H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether
  3. filtrationthe precipitate was filtered
  4. washwashed with ether
  5. customdried in air

Sources & evidence

ORD record
ord-daa927d7ed8f4ad086825775a4ad1448
Source dataset
uspto-grants-2013_09
Patent number
US08541453B2

Linked notes

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