Benzyl chloroformate → HCID 19866711, compound

HRID 232089Notes

Reaction equation

HRID 232089 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=1.[H-].[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[N:15]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 19866629HCID 19866629, compound

Product 1

HCID 19866711HCID 19866711, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[2-(2-Pyridyl)-phenyl thio]-1H-benzimidazole (0.825 mmole) in anhydrous dimethylformamide (15 ml) was treated under nitrogen with sodium hydride (0.90 mmole). The mixture was stirred for 20 minutes at room temperature, cooled to 5° and benzyl chloroformate (0.90 mmole) was added. The mixture was allowed to attain room temperature, then stirred for 18 hours after which it was poured into ice/water and extracted with ethyl acetate (2×15 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to an oil. The oil was flash chromatographed on silica gel using 10% ethyl acetate in dichloromethane as eluant to give the sub-title compound as a brown oil, MW 437 Base Peak 91.

Workup

  1. temperaturecooled to 5°
  2. customto attain room temperature
  3. stirringstirred for 18 hours after which it
  4. extractionextracted with ethyl acetate (2×15 ml)
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil
  9. customchromatographed on silica gel using 10% ethyl acetate in dichloromethane as eluant

Sources & evidence

ORD record
ord-ad0ef4a4c3624b5d92cc9ba1836784b7
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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