Hydrochloric Acid → N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)thiourea

HRID 1059875Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([NH:14][C:15]([NH:17]C(=O)C2C=CC=CC=2)=[S:16])[S:5][C:6]=1[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[N:3]=[C:4]([NH:14][C:15]([NH2:17])=[S:16])[S:5][C:6]=1[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)-N′-benzoylthiourea (700 mg) in methanol (7 ml) was added an aqueous sodium hydroxide solution (1N, 1.9 ml) dropwise. The mixture was stirred at 60° C. for 1 hour, cooled to ambient temperature, and the pH was adjusted to 8.0 with 1N hydrochloric acid. The mixture was diluted with water (50 ml) and stirred for 5 minutes. The precipitate was collected by filtration, washed with water and diisopropyl ether and dried under reduced pressure to give N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)thiourea (438 mg).

Workup

temperaturecooled to ambient temperature
stirringstirred for 5 minutes
filtrationThe precipitate was collected by filtration
washwashed with water and diisopropyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-bad9ac440c59413d90db3f8608f25679
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

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