Pyridine-3-sulfonyl chloride → 1-(pyridine-3-sulfonyl)-2-[[[3-methyl-4-(3-methoxypropoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole

HRID 411617Notes

Reaction equation

HRID 411617 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[Na].[CH3:12][C:13]1[C:14]([CH2:25][S:26]([C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)=[O:27])=[N:15][CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24]>C(N(CC)CC)C.ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([N:29]2[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=[C:28]2[S:26]([CH2:25][C:14]2[C:13]([CH3:12])=[C:18]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=[CH:16][N:15]=2)=[O:27])(=[O:9])=[O:8])[CH:2]=1

Participants

5

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chlorideHCID 9821387(S)-Rabeprazole sodium

Product 1

HCID 101959301-(pyridine-3-sulfonyl)-2-[[[3-methyl-4-(3-methoxypropoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazoleYield 50.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

100 mg of pyridine-3-sulfonyl chloride was added to 191 mg of 2-[[[3-methyl-4-(3-methoxypropoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole sodium salt in a mixture of 0.15 ml of triethylamine and 10 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight. Dichloromethane (20 ml) was added and washed with water, and 0.1M sodium bicarbonate solution. Organic layer was dried over anhydrous magnesium sulfate and evaporated. Residue was dissolved in minimum amounts of acetonitrile and ethyl ether was added for precipitation. Solids was collected and dried to give 127 mg of the titled product.

Workup

  1. washwashed with water, and 0.1M sodium bicarbonate solution
  2. dry with materialOrganic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. dissolutionResidue was dissolved in minimum amounts of acetonitrile and ethyl ether
  5. additionwas added for precipitation
  6. customSolids was collected
  7. customdried

Sources & evidence

ORD record
ord-3d0a29859a3b403ba17afe09cb5f5472
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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