Dimethylformamide → HCID 23364288, compound

HRID 1081511Notes

Reaction equation

HRID 1081511 reaction equation
[H-].[Na+].[CH:3]1([N:10]2[C:14]3[CH:15]=[C:16]([O:19][CH2:20][CH3:21])[CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[O:22])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.[CH3:28][O:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[C:34]([O:42][CH3:43])[CH:33]=1)=[O:31]>O>[CH:3]1([N:10]2[C:14]3[CH:15]=[C:16]([O:19][CH2:20][CH3:21])[CH:17]=[CH:18][C:13]=3[N:12]([S:38]([C:35]3[CH:36]=[CH:37][C:32]([C:30]([O:29][CH3:28])=[O:31])=[CH:33][C:34]=3[O:42][CH3:43])(=[O:40])=[O:39])[C:11]2=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22922587HCID 22922587, compoundHCID 23364278162141-56-2

Product 1

HCID 23364288HCID 23364288, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.095 g of sodium hydride as a 60% dispersion in oil is added to a mixture of 0.7 g of 3-cycloheptyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one and 50 ml of DMF and the mixture is stirred for 30 minutes at RT. 0.7 g of 4-methoxycarbonyl-2-methoxybenzenesulfonyl chloride is then added and the mixture is stirred overnight at RT. The reaction mixture is poured into iced water and the precipitate formed is filtered off and washed with water to give 0.9 g of the expected product, which is used as such in the next step.

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-a84732f0065949d2a36693bec6631ac9
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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