1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione → 2-[Benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetonitrile

HRID 1091679Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:14]#[N:15])[C:11]([NH2:13])=[NH:12].[F:16][C:17]([F:28])([F:27])[C:18](=O)[CH2:19][C:20](=O)[C:21]([CH3:24])([CH3:23])[CH3:22].[O-]CC.[Na+]>CS(C)=O.CC(=O)OCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:11]1[N:13]=[C:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[CH:19]=[C:18]([C:17]([F:16])([F:27])[F:28])[N:12]=1)[C:14]#[N:15]

Participants

Conditions

Temperature: 180 °C

Procedure

2-[Benzothiazol-2(3H)-ylidene]-2-cyanoacetamidine (0.2 g, 0.92 mmol) was dissolved in dimethylsulfoxide (1 mL), and 1,1,1-trifluoro-5,5,-dimethyl-2,4-hexanedione (320 μL, 1.84 mmol) and sodium ethoxide (0.6 mL of 21 wt % solution in ethanol, 1.84 mmol) were added. The solution was heated to 180° C. under microwave irradiation for 20 min, dissolved in EA, and washed with 1N hydrochloric acid and then water. Removal of the solvent gave 2-[benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetonitrile as a beige solid.

Workup

washwashed with 1N hydrochloric acid
customRemoval of the solvent

Sources & evidence

ORD record: ord-b98b75ea0af643d68097ea05af594a11
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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