Chloroacetonitrile → HCID 15037525, compound

HRID 1886414Notes

Reaction equation

HRID 1886414 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][CH:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:32][C:33]#[N:34]>CN(C)C=O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][CH:20]1[CH2:24][CH2:23][N:22]([CH2:32][C:33]#[N:34])[CH2:21]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 19875925HCID 19875925, compound

Product 1

HCID 15037525HCID 15037525, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred and heated (60° C.) suspension of 14 parts of 1-(2-pyridinylmethyl)-N-(3-pyrrolidinyl)-1H-benzimidazol-2-amine dihydrochloride and 9.5 parts of sodium carbonate in 113 parts of N,N-dimethylformamide were added dropwise 3.2 parts of 2-chloroacetonitrile. Upon completion, stirring was continued for 3 hours at 60° C. After cooling, the mixture was poured into ice water and the product was extracted six times with methylbenzene. The combined organic layers were washed with water, dried, filtered and evaporated, yielding 11 parts (87%) of 3-[[1-(2-pyridinylmethyl)-1H-benzimidazol-2-yl]amino]-1-pyrrolidineacetonitrile as a residue (compound 133).

Workup

  1. temperatureheated
  2. stirringUpon completion, stirring
  3. temperatureAfter cooling
  4. extractionthe product was extracted six times with methylbenzene
  5. washThe combined organic layers were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d5891465fb704f6abae0aff45bed5443
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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