N,N-Dimethylaniline → HCID 18535967, compound

HRID 411995Notes

Reaction equation

HRID 411995 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.[O:16]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=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:27][C:26]1[CH:25]=[CH:24][C:23]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 8764(4-Aminophenoxy)benzeneHCID 185358424-Chloro-6-nitroquinazoline--hydrogen chloride (1/1)

Product 1

HCID 18535967HCID 18535967, compoundYield 93.3%

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-phenoxyaniline (926 mg, 5 mmol) and N,N-dimethylaniline (1.215 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-phenoxyanilino)quinazoline hydrochloride (1.702 g, 86%) as an orange solid; mp 293-294° 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-8c30eb1f85ac4ee5993506ff6338e1ac
Source dataset
uspto-grants-2003_05
Patent number
US06562818B1

Reaction notes

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