Phenyl isocyanate → N1-(N'-phenylcarbamoyl)-5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 2248441Notes

Reaction equation

HRID 2248441 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]1[O:34][C:33]2[C:12](=[CH:13][C:14]3[N:18]=[C:17]([S:19]([CH2:21][C:22]4[C:27]([CH3:28])=[C:26]([O:29][CH3:30])[C:25]([CH3:31])=[CH:24][N:23]=4)=[O:20])[NH:16][C:15]=3[CH:32]=2)[O:11]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([NH:7][C:8]([N:16]2[C:15]3[CH:32]=[C:33]4[O:34][CH2:10][O:11][C:12]4=[CH:13][C:14]=3[N:18]=[C:17]2[S:19]([CH2:21][C:22]2[C:27]([CH3:28])=[C:26]([O:29][CH3:30])[C:25]([CH3:31])=[CH:24][N:23]=2)=[O:20])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 212958635,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Product 1

HCID 53654244N1-(N'-phenylcarbamoyl)-5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylisocyanate (0.20 g, 0.00167 mol) dissolved in CH2Cl2 (5 ml) was added dropwise under stirring to a solution of 5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (0.50 g, 0.00139 mol) and triethylamine (0.28 g, 0.00278 mol) in CH2CL2 (15 ml). The mixture was then stirred at room temperature for 50 hours. The CH2Cl2 -solution was washed with water, dried (MgSO4) and the solvent was evaporated giving the desired product as an oil (0.03 g, 5%). NMR data for the final product is given below.

Workup

  1. additionwas added dropwise
  2. washThe CH2Cl2 -solution was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9c2e9a64e5fa4f8aa1a4e807c172b390
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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