Ammonium Hydroxide → 2-Amino-7-nitro-6-trifluoromethoxybenzothiazole

HRID 865794Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]([F:18])([F:17])[F:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[NH4+:20]>C(O)C>[NH2:20][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]([F:18])([F:17])[F:16])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 0.4 g of 2-chloro-7-nitro-6-trifluoromethoxybenzothiazole and 10 cm3 of 33% aqueous ammonium hydroxide solution in 30 cm3 of ethanol is heated at 110° C. in an autoclave for 5 hours. The mixture is cooled and the solvent is evaporated off under reduced pressure (2.7 kPa). After purification by flash chromatography on silica with a cyclohexane/ethyl acetate mixture (4/6 by volume) as eluent, 0.22 g of 2-amino-7-nitro-6-trifluoromethoxybenzothiazole is obtained, melting at 180° C.

Workup

temperatureThe mixture is cooled
customthe solvent is evaporated off under reduced pressure (2.7 kPa)
customAfter purification by flash chromatography on silica with a cyclohexane/ethyl acetate mixture (4/6 by volume) as eluent

Sources & evidence

ORD record: ord-15785466c0fe416883f033db3706f711
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05567822

Reaction notes

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