Methanol → 1-Benzothiazol-6-yl-1,3-dihydro-imidazol-2-one

HRID 2383867Notes

Reaction equation

OS(O)(=O)=O.[S:6]1[C:10]2[CH:11]=[C:12]([NH:15][C:16]([NH:18][CH2:19][CH:20](OC)OC)=[O:17])[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.CO.[OH-].[K+]>C(Cl)(Cl)Cl>[S:6]1[C:10]2[CH:11]=[C:12]([N:15]3[CH:20]=[CH:19][NH:18][C:16]3=[O:17])[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

1N H2SO4 (2 mL) was added to 1-benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea (I-142a: 300 mg) and the resulting mixture was stirred at 0° C. for 30 minutes. The reaction mixture was heated to 50° C. for 2 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was cooled to 0° C. and basified with 10% KOH solution. The precipitate was collected, washed with water and dried under reduced pressure to afford 170 mg of 1-Benzothiazol-6-yl-1,3-dihydro-imidazol-2-one (73.59% yield).

Workup

temperatureThe reaction mixture was heated to 50° C. for 2 hours
customThe precipitate was collected
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-428d8b92dc534f348a09e9da058b4d0a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263635B2

Reaction notes

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