Sodium Chloride → HCID 9893626, compound

HRID 378715Notes

Reaction equation

HRID 378715 reaction equation
[CH2:1]([O:3][CH:4]([O:27][CH2:28][CH3:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:26])[CH3:2].CC(C)([O-])C.[K+].[C:36]1([CH3:47])[CH:41]=[CH:40][C:39]([NH:42][C:43](=[O:46])[CH2:44]Br)=[CH:38][CH:37]=1.[Cl-].[Na+]>CS(C)=O>[CH2:28]([O:27][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:44][C:43]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([CH3:47])=[CH:37][CH:38]=2)=[O:46])([NH:15][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[O:17])[C:7]1=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 947222-Bromo-N-(4-methylphenyl)acetamideHCID 11014797HCID 11014797, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9893626HCID 9893626, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of 0.397 g of (RS)-1-(2,2-diethoxyethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one in 4 ml of dry dimethyl sulfoxide was added 1 ml of a 1M solution of potassium t-butoxide in dry dimethyl sulfoxide at room temperature under a nitrogen atmosphere, followed by stirring for 30 minutes. To the mixture was added dropwise a solution of 0.228 g of N-p-tolyl-2-bromoacetamide in 2 ml of dry dimethyl sulfoxide, followed by stirring at the same temperature for 30 minutes. The reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl ether. The ethyl ether layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 0.35 g (65%) of the title compound.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. extractionextracted with ethyl ether
  3. dry with materialThe ethyl ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-25aac06efb73485d9f8a4f4505e08615
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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