Potassium Carbonate → 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile

HRID 1091669Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[SH:11].CS[C:14](SC)=[C:15]([C:18]1[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=1)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.C(O)C.C(Cl)Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]2[NH:1][C:14](=[C:15]([C:18]3[N:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:21]=[CH:20][N:19]=3)[C:16]#[N:17])[S:11][C:3]=2[CH:4]=1)([OH:8])=[O:7]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-amino-3-mercaptobenzoic acid (768 mg, 4.5 mmol), 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (1.45 g, 5.0 mmol, 1.1 eq.), 4-dimethylaminopyridine (550 mg, 4.5 mmol, 1 eq.), and potassium carbonate (622 mg, 4.5 mmol, 1 eq.) in ethanol (20 mL) was heated at 160° C. for 0.4 hr in a microwave. The mixture was cooled to room temperature, diluted with DCM, and washed with 1M hydrochloric acid. The DCM fraction was decanted, filtered, and concentrated under vacuum to give 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile (729 mg, 40% yield) as a brown solid.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with 1M hydrochloric acid
customThe DCM fraction was decanted
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b32016c9a04f42898ca8ce3fbc4e6282
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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