Dimethylformamide → HCID 23364281, compound

HRID 1081508Notes

Reaction equation

HRID 1081508 reaction equation
[H-].[Na+].[CH:3]1([N:9]2[C:13]3[CH:14]=[C:15]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:16]=[CH:17][C:12]=3[NH:11][C:10]2=[O:23])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.[CH3:29][O:30][C:31]([C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[C:35]([O:43][CH3:44])[CH:34]=1)=[O:32]>O>[CH:3]1([N:9]2[C:13]3[CH:14]=[C:15]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:16]=[CH:17][C:12]=3[N:11]([S:39]([C:36]3[CH:37]=[CH:38][C:33]([C:31]([O:30][CH3:29])=[O:32])=[CH:34][C:35]=3[O:43][CH3:44])(=[O:41])=[O:40])[C:10]2=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22922494HCID 22922494, compoundHCID 23364278162141-56-2

Product 1

HCID 23364281HCID 23364281, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.095 g of sodium hydride as a 60% dispersion in oil is added in portions to a mixture of 0.7 g of 3-cyclohexyl-1,3-dihydro-5-(2-methoxyethoxy)-2H-benzimidazol-2-one and 50 ml of DMF and the mixture is stirred for 30 minutes at RT. 0.6 g of 4-methoxycarbonyl-2-methoxybenzenesulfonyl chloride is then added and the mixture is stirred for two hours at RT. The reaction mixture is poured into a mixture of water and ice, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 0.8 g of the expected product, which is used as such in the next step.

Workup

  1. stirringthe mixture is stirred for two hours at RT
  2. extractionextracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-b78a1fc61b5d4bc490e39e922b26f16f
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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