Hydrochloric Acid → HCID 66593539, compound

HRID 1091661Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][CH:9]1[CH2:17][C:18]#[N:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:23]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=1.Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[C:17]([C:23]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=1)[C:18]#[N:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[1-(tert-butoxycarbonyl)benzimidazol-2(3H)-yl]acetonitrile (6 g, 23 mmol) in THF (50 mL) was added to a suspension of 60% sodium hydride in mineral oil (1.38 g, 35 mmol) in tetrahydrofuran (85 mL) at 0° C. over 10 min. The suspension was stirred at 0° C. for 15 min, and 2-chloro-4-trifluoromethylpyrimidin (2.79 mL, 23 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight, and water (300 mL) and then 1N hydrochloric acid (40 mL) were added. The crude product was extracted into chloroform and washed twice with water (100 mL each). The organic phase was dried over magnesium sulfate, and the solvent was removed under vacuum to give 2-[1-(tert-butoxycarbonyl)benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (8.17 g) as a brown oil.

Workup

temperatureto warm to room temperature
stirringstirred overnight
extractionThe crude product was extracted into chloroform
washwashed twice with water (100 mL each)
dry with materialThe organic phase was dried over magnesium sulfate
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-b1a3f2a45753420c9ece608542f34031
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129396B2

Reaction notes

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