Water → 5-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethyl-N-methylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

HRID 965556Notes

Reaction equation

HRID 965556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6](=[O:28])[C:5]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[N:29]([CH3:31])[CH3:30].[H-].[Na+].[CH3:41]I.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([N:20]([CH3:41])[C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22])=[CH:18][CH:19]=1)(=[O:13])=[O:12])[C:6](=[O:28])[C:5]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[N:29]([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 190765585-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

Product 1

HCID 190766165-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethyl-N-methylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.420 g of the compound obtained in EXAMPLE 30 in 7 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.027 g of sodium hydride as an 80% dispersion in oil is added. After stirring for 30 minutes, 0.05 ml of methyl iodide is added and the reaction mixture is stirred for 10 minutes. It is poured into water, extracted with AcOEt, washed with water, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=0.211 g. M.p.=145°-148° C.

Workup

  1. stirringthe reaction mixture is stirred for 10 minutes
  2. extractionextracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum
  6. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-b2055b7e77044096ba77edd00f3c42c2
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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