P-Anisidine → 4-(4'-Methoxyanilino)-7-trifluoromethylquinazoline

HRID 2059195Notes

Reaction equation

HRID 2059195 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1>C(O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 128067424-Chloro-7-(trifluoromethyl)quinazoline

Product 1

HCID 128067754-(4'-Methoxyanilino)-7-trifluoromethylquinazolineYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of ethanol were added to a mixture of 2.3 g of 4-chloro-7-trifluoromethylquinazoline and 1.4 g of p-anisidine. The resulting mixture was heated to dissolve the solids, whereupon the solution solidified immediately. After cooling, the resulting crystals were collected by filtration and washed with, in turn, ethanol, dilute aqueous sodium hydroxide and water. The resulting crystals were recrystallized from ethanol, to give 2.5 g (yield 78%) of the desired Compound No. 51 in the form of colourless needles melting at 190°-194° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. dissolutionto dissolve the solids
  3. temperatureAfter cooling
  4. filtrationthe resulting crystals were collected by filtration
  5. washwashed with, in turn, ethanol, dilute aqueous sodium hydroxide and water
  6. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-d53d93b40fc149e7a6862c357427ee91
Source dataset
uspto-grants-1982_03
Patent number
US04322420

Reaction notes

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