N,N-Dimethylaniline → HCID 18535765, compound

HRID 411999Notes

Reaction equation

HRID 411999 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[N:6]=[CH:5][N:4]=1.[CH2:16]([O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C1C=CC=CC=1>C(O)(C)C>[ClH:2].[NH2:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[CH:5][N:4]=[C:3]2[NH:28][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 228604-BenzyloxyanilineHCID 185358424-Chloro-6-nitroquinazoline--hydrogen chloride (1/1)

Product 1

HCID 18535765HCID 18535765, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of crude 4-chloro-6-nitroquinazoline hydrochloride (5 mmol) (Morley J. S. and Simpson J. C. E., J. Chem. Soc., 1948: 360) was refluxed under nitrogen with stirring in isopropanol (10 mL) containing 4-benzyloxyaniline (999 mg, 5 mmol) and N,N-dimethylaniline (1.209 g, 10 mmol) for 3 hours. The mixture was allowed to cool to 25° C., and the precipitate was collected by Buchner filtration, rinsed with isopropanol (2×10 mL), and dried at 60° C. in a vacuum oven to give 6-amino-4-(4-benzyloxyanilino)quinazoline hydrochloride (1.675 g, 82%) as a mustard yellow solid; mp 246-248° C.

Workup

  1. temperaturewas refluxed under nitrogen
  2. filtrationthe precipitate was collected by Buchner filtration
  3. washrinsed with isopropanol (2×10 mL)
  4. customdried at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-c593f4a7441449a69f375c105d8d7350
Source dataset
uspto-grants-2003_05
Patent number
US06562818B1

Reaction notes

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