Thiourea → 5-[4-Chloro-3-(methylsulfonyl)phenyl]-4-methyl-1,3-thiazol-2-amine

HRID 1689569Notes

Reaction equation

Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=1)[C:3](=O)[CH3:4].[NH2:17][C:18]([NH2:20])=[S:19]>C(O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[S:19][C:18]([NH2:20])=[N:17][C:3]=2[CH3:4])=[CH:7][C:8]=1[S:13]([CH3:16])(=[O:15])=[O:14]

Participants

Conditions

Temperature: 70 °C

Procedure

1-bromo-1-(4-chloro-3-methanesulfonyl-phenyl)-propan-2-one (480 mg 1.5 mmol) and thiourea (114 mg 1.5 mmol) were combined in ethanol (12 ml) and heated to 70° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and the solid product was collected by filtration and dried under vacuum to yield 5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine as an off-white solid (375 mg). 1H NMR (400 MHz DMSO-d6) δ 9.4 (br s, 2H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (dd, 1H), 3.4 (s, 3H), 2.3 (s, 3H).

Workup

temperatureto cool to room temperature
filtrationthe solid product was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-890750b43bba4d7b8d7e244d5f84a0f2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153389B2

Reaction notes

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