Water → HCID 178484611, compound

HRID 2109024Notes

Reaction equation

HRID 2109024 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6](=[C:14](OCC)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]1=[O:24])(=O)C.[CH3:25][N:26]([CH3:38])[C:27]([CH2:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1)=[O:28].O>CN(C)C=O>[CH3:25][N:26]([CH3:38])[C:27]([CH2:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37]/[C:14](=[C:6]2\[C:5](=[O:24])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=3)/[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:33][CH:32]=1)=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 11528502HCID 11528502, compoundHCID 69061213HCID 69061213, compound

Product 1

HCID 178484611HCID 178484611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6.0 g of 1-acetyl-3-(1-ethoxy-1-phenylmethylen)-6-chloro-2-indolinone (educt IX) and 3.9 g of N-(dimethylcarbamoylmethyl)-p-phenylenediamine (educt XV.208) are dissolved in 50 ml of dimethylformamide and stirred for 4.5 hours at 120° C. After cooling water is added, the precipitate formed is suction filtered and washed with methanol. The product is purified through a silica gel column with methylene chloride/methanol (100:1) as eluant and finally recrystallised from ether.

Workup

  1. additionis added
  2. customthe precipitate formed
  3. filtrationfiltered
  4. washwashed with methanol
  5. customThe product is purified through a silica gel column with methylene chloride/methanol (100:1) as eluant
  6. customfinally recrystallised from ether

Sources & evidence

ORD record
ord-8775a0fca40444739f4b7f70e9aeff09
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

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