Sulfuric Acid → HCID 86630626, compound

HRID 643719Notes

Reaction equation

HRID 643719 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([CH3:21])(O)[CH3:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3][CH2:2]1.C[Si]([C:31]#[N:32])(C)C.S(=O)(=O)(O)[OH:34].C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([NH:32][CH:31]=[O:34])([CH3:19])[CH3:21])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 11501747HCID 11501747, compound

Product 1

HCID 86630626HCID 86630626, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-2-ol (Step E, 996 mg, 2.63 mmol) and trimethylsilyl cyanide (1.4 mL, 10.5 mmol) was added sulfuric acid (3 mL) at −30° C. The whole was warm to room temperature and stirred for 18 h. To the reaction mixture was added water at 0° C. and stirred for 1 h. Then, the resulting mixture was poured into potassium carbonate aqueous solution (20 mL) at 0° C. and extracted with dichloromethane (30 mL×3). The combined organic layer was dried over sodium sulfate and concentrated to afford the title compound (330 g, 31%) as a white amorphous.

Workup

  1. stirringstirred for 1 h
  2. extractionextracted with dichloromethane (30 mL×3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a9e530da347481982c6de16dd46ef1e
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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