Ethyl Acetate → 2-(6-nitrobenzothiazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile

HRID 1091672Notes

Reaction equation

CS[C:3]1[S:4][C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][C:24]#[N:25])[N:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)OCC>C(O)C>[N+:12]([C:10]1[CH:9]=[CH:8][C:6]2[NH:7][C:3](=[C:23]([C:19]3[N:18]=[C:17]([C:16]([F:27])([F:15])[F:26])[CH:22]=[CH:21][N:20]=3)[C:24]#[N:25])[S:4][C:5]=2[CH:11]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 2-(methylthio)-6-nitro-1,3-benzothiazole (226 mg, 1.0 mmol) in ethanol (3.5 mL) was added 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (187 mg, 1.0 mmol) and potassium carbonate (207 mg, 1.5 mmol). The orange mixture was heated in the microwave at 160° C. for 15 min, then cooled and poured into EA (60 mL). The organic layer was washed twice with 1N hydrochloric acid (25 mL each), brine (25 mL), and water (5 mL), then dried with magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-(6-nitrobenzothiazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (349 mg, 96% yield) as a yellow solid.

Workup

temperaturecooled
washThe organic layer was washed twice with 1N hydrochloric acid (25 mL each), brine (25 mL), and water (5 mL)
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-de4496d4cb5942b3ba948d9a4088c081
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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