Ammonium Chloride → 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

HRID 1295243Notes

Reaction equation

HRID 1295243 reaction equation
C(O[K])(C)(C)C.C1(C)C=CC(S([CH2:16][N+:17]#[C-])(=O)=O)=CC=1.[CH2:20]([N:27]1[CH:31]=[C:30]([CH:32]=O)[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(COC)OC.CO>[CH2:20]([N:27]1[CH:31]=[C:30]([CH2:32][C:16]#[N:17])[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehydeHCID 178418922HCID 178418922, compound

Product 1

HCID 693145121-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrileYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a mixture of t-butoxy potassium (11.2 g) and dimethoxyethane (50 ml) was added a solution of p-toluenesulfonylmethyl isocyanide (10.3 g) in dimethoxyethane (50 ml) at −78° C. and the mixture was stirred for 5 min. Then a solution of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (14.6 g) in dimethoxyethane (50 ml) was added. After stirring at said temperature for 1 hr, the mixture was stirred for 1 hr. while raising the temperature to room temperature. To the obtained mixture was added methanol (150 ml), and the mixture was refluxed for 1 hr. After cooling, the reaction solution was poured into saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.1 g, yield 86%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. stirringAfter stirring
  2. customfor 1 hr
  3. stirringthe mixture was stirred for 1 hr
  4. temperaturethe mixture was refluxed for 1 hr
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f10f239a75044880a46649b784245bab
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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