Dimethylformamide → HCID 23364284, compound

HRID 1081507Notes

Reaction equation

HRID 1081507 reaction equation
[H-].[Na+].[CH:3]1([N:9]2[C:13]3[CH:14]=[C:15]([O:18][CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][C:12]=3[NH:11][C:10]2=[O:24])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.[CH3:30][O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[C:36]([O:44][CH3:45])[CH:35]=1)=[O:33]>O.C1COCC1>[CH:3]1([N:9]2[C:13]3[CH:14]=[C:15]([O:18][CH:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)[CH:16]=[CH:17][C:12]=3[N:11]([S:40]([C:37]3[CH:38]=[CH:39][C:34]([C:32]([O:31][CH3:30])=[O:33])=[CH:35][C:36]=3[O:44][CH3:45])(=[O:42])=[O:41])[C:10]2=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22922524HCID 22922524, compoundHCID 23364278162141-56-2

Product 1

HCID 23364284HCID 23364284, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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-5-cyclopentoxy-1,3-dihydro-2H-benzimidazol-2-one, 50 ml of DMF and 50 ml of THF 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 18 hours at RT. The reaction mixture is poured into a mixture of water and ice and the precipitate formed is filtered off and washed with water and then with heptane to give 1 g of the expected product, which is used as such in the next step.

Workup

  1. stirringthe mixture is stirred for 18 hours at RT
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-f8fdca79f41b42dc91849f766ede4dcf
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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