p-Toluidine → HCID 22013091, compound

HRID 378709Notes

Reaction equation

HRID 378709 reaction equation
O[C:2]([CH2:4][C:5]1([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:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14])=[O:3].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH2:51][C:52]1[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=1>CN(C)C=O>[CH3:58][C:55]1[CH:56]=[CH:57][C:52]([NH:51][C:2]([CH2:4][C:5]2([NH:15][C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)=[O:17])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]2=[O:14])=[O:3])=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 22013003HCID 22013003, compound

Product 1

HCID 22013091HCID 22013091, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.150 g of (RS)-3-(hydroxycarbonylmethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one and 0.103 g of dicyclohexylcarbodiimide in 10 ml of N,N-dimethylformamide were added successively 0.074 g of 1-hydroxybenzotriazole and 0.052 g of p-toluidine. The resulting mixture was stirred at room temperature for 18 hours, followed by concentration. The residue was diluted with ethyl acetate and washed successively with dilute hydrochloric acid and saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (chloroform/methanol=20/1) to obtain 0.083 g (44%) of the title compound as a white powder.

Workup

  1. concentrationfollowed by concentration
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed successively with dilute hydrochloric acid and saturated aqueous sodium hydrogencarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-dbaf8a0e89ac4c678553932a45fa20d5
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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