Triethylamine → N-methoxycarbonyl-5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 2248440Notes

Reaction equation

HRID 2248440 reaction equation
C[C:2]([O:4]Cl)=[O:3].[CH2:6]1[O:30][C:29]2[C:8](=[CH:9][C:10]3[N:14]=[C:13]([S:15]([CH2:17][C:18]4[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=4)=[O:16])[NH:12][C:11]=3[CH:28]=2)[O:7]1.[CH2:31](N(CC)CC)C>C(Cl)Cl>[CH3:31][O:4][C:2]([N:12]1[C:11]2[CH:28]=[C:29]3[O:30][CH2:6][O:7][C:8]3=[CH:9][C:10]=2[N:14]=[C:13]1[S:15]([CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=1)=[O:16])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12616564Chloro methylformateHCID 212958635,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Product 1

HCID 19996494N-methoxycarbonyl-5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloro methylformate (0.24 g, 0.0026 mol) dissolved in CH2Cl2 (5 ml) was added dropwise to a stirred solution of 5,6-methylenedioxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (0.80 g, 0.0022 mol) and triethylamine in CH2Cl2 (10 ml). The mixture was then stirred at room temperature for 19 h. The CH2Cl2 -solution was washed with water, dried (MgSO4) and the solvent was evaporated giving the desired product as an oil (0.06 g, 6%). NMR data for the final product is given below.

Workup

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

Sources & evidence

ORD record
ord-b0a0a202695f4d1ba74cd04fb694d5ff
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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