Water → 2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

HRID 1091673Notes

Reaction equation

[N+:1]([C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9](=[C:11]([C:14]3[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)[C:12]#[N:13])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[OH2:26]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9](=[C:11]([C:14]3[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)[C:12]([NH2:13])=[O:26])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(6-Nitrobenzothiazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (296 mg, 0.81 mmol) was dissolved in concentrated sulfuric acid (3.0 mL). The reddish mixture was stirred at 50° C. for 8 hr, then poured into cold water (25 mL). The yellow precipitate was collected by filtration, washed with hexanes (30 mL), and dried under vacuum to give 2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (280 mg, 89% yield) as an orange solid.

Workup

filtrationThe yellow precipitate was collected by filtration
washwashed with hexanes (30 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-798edc4405084e0b8b2804b5113dc9e2
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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