Tetrahydrofuran → HCID 123151891, compound

HRID 1747830Notes

Reaction equation

HRID 1747830 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1COCC1.Br[CH2:28][C:29]#[N:30]>O>[C:29]([CH2:28][N:12]([C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9][CH:10]=1)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])#[N:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 123920024HCID 123920024, compound

Product 1

HCID 123151891HCID 123151891, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl (1-phenyl-1H-pyrazol-5-yl)carbamate (3.80 g), 60% NaH (0.422 g) and THF (60.0 mL) was added bromoacetonitrile (1.93 g) at room temperature, and the mixture was stirred for 30 min. To the reaction mixture was added water, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (4.38 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b10b6529130a40f2bd6251d87003024d
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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