Water → HCID 67716628, compound

HRID 266161Notes

Reaction equation

HRID 266161 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:17][C:18]1[N:27]=[C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=2)[C:25]2[C:20](=[CH:21][C:22]([O:40][CH3:41])=[C:23]([O:38][CH3:39])[CH:24]=2)[N:19]=1.O>CN(C)C=O>[C:10]1([N:9]([CH2:17][C:18]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=3)[C:25]3[C:20](=[CH:21][C:22]([O:40][CH3:41])=[C:23]([O:38][CH3:39])[CH:24]=3)[N:19]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11487DiphenylamineHCID 24758Sodium hydrideHCID 107856562-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

Product 1

HCID 67716628HCID 67716628, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (oily, 60%, 0.129 g) was added to a solution of diphenylamine (0.497 g) in N,N-dimethylformamide (10 ml), and the mixture was stirred at room temperature for 20 minutes. Then, 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (1.0 g) was added, and the mixture was stirred at 100° C. for 4 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate - hexane (1:1, v/v) gave 2-(N,N-diphenylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (0.27 g, 20%). This compound was recrystallized from ethyl acetate - hexane. Colorless prisms, mp. 215°-216° C.

Workup

  1. stirringthe mixture was stirred at 100° C. for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe fractions eluted with ethyl acetate - hexane (1:1

Sources & evidence

ORD record
ord-806c2db3d48a413db6eb0ab188b8fe40
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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