Hydrochloric Acid → HCID 18631033, compound

HRID 1060027Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH:16][C:17]([NH2:19])=[S:18].[H-].[Na+].[ClH:22]>CS(C)=O.C(OCC)(=O)C.O1CCOCC1>[ClH:22].[ClH:22].[NH2:19][C:17]1[S:18][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=3)=[CH:4][C:3]=2[N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of N-(2-fluoro-5-(4-methoxypyridin-2-yl)phenyl)-thiourea (0.104 g) in dimethyl sulfoxide (5 ml) was added a sodium hydride (60% dispersion in mineral oil ,15.4 mg), and the mixture was stirred at 100° C. for 5 hours. The mixture was diluted with ethyl acetate and washed with water three times and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 10 g, 5% methanol in dichloromethane). The compound obtained was dissolved in ethyl acetate, and a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) was added. The precipitate was collected by filtration and dried under reduced pressure to give 2-amino-5-(4-methoxypyridin-2-yl)benzothiazole dihydrochloride (46 mg).

Workup

washwashed with water three times and brine
dry with materialThe separated organic layer was dried over sodium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography (silica gel 10 g, 5% methanol in dichloromethane)
customThe compound obtained
filtrationThe precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-03b030064464451997103a52e79eea9e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

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