3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoroanilino)-6-(1-imidazolyl)quinazoline

HRID 618671Notes

Reaction equation

HRID 618671 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH2:21].[OH-].[NH4+]>C(O)(C)C.O>[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 14923Ammonium HydroxideHCID 218478354-Chloro-6-(1-imidazolyl)quinazoline

Product 1

HCID 218478184-(3-Chloro-4-fluoroanilino)-6-(1-imidazolyl)quinazolineYield 19.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-(1-imidazolyl)quinazoline (3.8 g) and 3-chloro-4-fluoroaniline (2.64 g) in isopropanol (50 ml) was heated to reflux for 3 hours. The solid product so obtained was filtered off, washed with isopropanol and with diethyl ether and dried. The solid so obtained was suspended in water (40 ml) and an aqueous ammonium hydroxide solution (15 ml) was added. The mixture was stirred for 10 minutes. the solid was filtered off, washed with 20% aqueous ammonium hydroxide solution, with water, with acetone and with diethyl ether and dried to give 4-(3-chloro-4-fluoroanilino)-6-(1-imidazolyl)quinazoline (1.10 g); NMR Spectrum: (CD3SOCD3) 7.22 (s, 1H), 7.49 (t, 1H), 7.84 (m, 1H), 7.88 (s, 1H), 7.96 (d, 1H), 8.19 (t, 1H), 8.24 (m, 1H), 8.40 (s, 1H), 8.68 (s, 1H), 8.74 (d, 1H), 9.90 (s, 1H);

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customThe solid product so obtained
  4. filtrationwas filtered off
  5. washwashed with isopropanol and with diethyl ether
  6. customdried
  7. customThe solid so obtained
  8. filtrationthe solid was filtered off
  9. washwashed with 20% aqueous ammonium hydroxide solution, with water, with acetone and with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-5933c9103f02475195a196f2ec7770e7
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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