Water → 12-amino-3-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

HRID 649953Notes

Reaction equation

[Sn](Cl)Cl.[F:4][C:5]1[CH:6]=[CH:7][C:8]2[C:12]([C:13]#[N:14])=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)[S:10][C:9]=2[CH:25]=1.O>Cl.C(O)C>[NH2:14][C:13]1[C:12]2[C:8]3[CH:7]=[CH:6][C:5]([F:4])=[CH:25][C:9]=3[S:10][C:11]=2[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Tin(II) chloride (50 g) was dissolved in a 18% hydrochloric acid (250 ml) solution heated to 50° C., and a suspension of 6-fluoro-2-(2-nitroanilino)benzo[b]thiophene-3-carbonitrile (20 g) in ethanol (280 ml) was added. The mixture was refluxed under heating for 4 hours. Then, the reaction mixture was cooled to 40° C. and poured into water (1 L) and the mixture was stood still for 30 minutes. The precipitated crystals were filtered by suction and washed with water (500 ml) to give 12-amino-3-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine.1 hydrochloride (15 g).

Workup

additionwas added
temperatureThe mixture was refluxed
temperatureunder heating for 4 hours
temperatureThen, the reaction mixture was cooled to 40° C.
filtrationThe precipitated crystals were filtered by suction
washwashed with water (500 ml)

Sources & evidence

ORD record: ord-f94359bd81404aea8e59f99343368191
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271225B1

Reaction notes

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