Hydrochloric Acid → 7-Chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochloride

HRID 2227924Notes

Reaction equation

HRID 2227924 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1.Cl>CC(O)C.CC(C)=O>[ClH:1].[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:21][C:20]3[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][C:19]=3[F:24])=[N:3][CH:4]=[N:5]2)=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 938984-Chloro-2-fluoroanilineHCID 104904554,7-Dichloro-6-nitroquinazoline

Product 1

HCID 224782507-Chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4,7-dichloro-6-nitroquinazoline (24.4 g, 0.1 mol), 4-chloro-2-fluoroaniline and ethereal hydrogen chloride (100 ml of a 1M solution) in 2-propanol (600 ml) was heated at reflux for 1.5 hours. The mixture was allowed to cool and diluted with acetone. The solid product was collected by filtration, washed with acetone and dried to give 7-chloro-4-(4-chloro-2-fluoroanilino)-6nitroquinazoline hydrochloride (35.0 g, 90%) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationThe solid product was collected by filtration
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-a9a5ec8f58e0484cb5424a056aad3619
Source dataset
uspto-grants-2002_07
Patent number
US06414148B1

Reaction notes

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