Hydrochloric Acid → N-(3-chloro-4-fluorophenyl)-5,7-difluoroquinazolin-4-amine

HRID 1442979Notes

Reaction equation

HRID 1442979 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([F:23])=[CH:19][C:20]=2[F:22])[N:15]=[CH:14][N:13]=1>O1CCOCC1.CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:12]2[C:21]3[C:16](=[CH:17][C:18]([F:23])=[CH:19][C:20]=3[F:22])[N:15]=[CH:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 97083-Chloro-4-fluoroanilineHCID 534026004-Chloro-5,7-difluoroquinazoline

Product 1

HCID 68676704N-(3-chloro-4-fluorophenyl)-5,7-difluoroquinazolin-4-amineYield 71.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-4-fluoroaniline (12 g) and 1N HCl in dioxane (40 ml) were added sequentially, each in one portion, to a mixture of 4-chloro-5,7-difluoroquinazoline (16.5 g) in IPA (250 ml) and the mixture was stirred at 80° C. under a nitrogen atmosphere for 17 hours. The reaction mixture was cooled to 0° C. and the precipitated solid was filtered and dried to leave N-(3-chloro-4-fluorophenyl)-5,7-difluoroquinazolin-4-amine as a green solid (18.2 g, 71%); Mass spectrum MH+ 310.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe precipitated solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-19694bcb96cb47fc97ac954b05ee04b2
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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