Dimethylformamide → HCID 23364248, compound

HRID 1081512Notes

Reaction equation

HRID 1081512 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[NH:10][C:11](=[O:19])[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:8]=2[CH:7]=1)[CH3:4].CN(C=O)C.[CH3:27][O:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[C:33]([O:41][CH3:42])[CH:32]=1)=[O:30]>C1COCC1>[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[N:10]([S:37]([C:34]3[CH:35]=[CH:36][C:31]([C:29]([O:28][CH3:27])=[O:30])=[CH:32][C:33]=3[O:41][CH3:42])(=[O:39])=[O:38])[C:11](=[O:19])[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:8]=2[CH:7]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 23364278162141-56-2HCID 54505929HCID 54505929, compound

Product 1

HCID 23364248HCID 23364248, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.2 g of sodium hydride as a 60% dispersion in oil is added to a mixture of 1 g of 5-ethoxy-1,3-dihydro-3-(pyrid-2-yl)-2H-benzimidazol-2-one, 25 ml of DMF and 25 ml of THF and the mixture is stirred for 30 minutes at RT. 1 g of 4-methoxycarbonyl-2-methoxybenzenesulfonyl chloride is then added and the mixture is stirred for 3 hours at RT. The reaction mixture is concentrated under vacuum, the residue is taken up with water, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 1 g of the expected product, which is used as such in the next step.

Workup

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

Sources & evidence

ORD record
ord-74aee3ef0cd842598524007495667838
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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