Water → HCID 23364251, compound

HRID 1081499Notes

Reaction equation

HRID 1081499 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[NH:8][C:9](=[O:18])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:6]=2[CH:5]=1.[CH2:21]([N:23]([CH2:37][CH3:38])[C:24](=[O:36])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[CH3:22].O>CN(C=O)C>[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[N:8]([S:32]([C:29]3[CH:28]=[CH:27][C:26]([NH:25][C:24]([N:23]([CH2:37][CH3:38])[CH2:21][CH3:22])=[O:36])=[CH:31][CH:30]=3)(=[O:34])=[O:33])[C:9](=[O:18])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27582454-(3,3-Diethyl-ureido)-benzenesulfonyl chlorideHCID 30617862H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-(2-chlorophenyl)-

Product 1

HCID 23364251HCID 23364251, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.075 g of sodium hydride as a 60% dispersion in oil is added to a solution of 0.5 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-2H-benzimidazol-2-one in 40 ml of DMF and the mixture is stirred for 30 minutes at RT. 0.6 g of 4-(N',N'-diethylureido)benzenesulfonyl chloride is then added and the mixture is stirred for 4 hours at RT. The reaction mixture is poured into iced water, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give 0.45 g of the expected product. M.p.=222° C.

Workup

  1. stirringthe mixture is stirred for 4 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
  6. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-7d0f1ecffc4b4e1ba66db14150469457
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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