Water → 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

HRID 1091667Notes

Reaction equation

[C: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])[NH:10][C:6]=2[CH:5]=1)([OH:3])=[O:2].[OH2:26]>S(=O)(=O)(O)O>[C: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:21])[F:22])[CH:17]=[CH:16][N:15]=3)[C:12]([NH2:13])=[O:26])[NH:10][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)-acetonitrile (450 mg, 1.29 mmol) from the previous step, dissolved in concentrated sulfuric acid (2 mL), was heated to 50° C. for 6 hr. The mixture was cooled to room temperature and added dropwise to rapidly stirred room-temperature water (500 mL). The precipitate that formed was collected by filtration, washed with water, and dried under vacuum to give 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (322 mg, 0.88 mmol, 68% yield) as a dark brown solid.

Workup

temperatureThe mixture was cooled to room temperature
customThe precipitate that formed
filtrationwas collected by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-85e0ddfccc724bf3a8bc14209c6eedec
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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