Aniline → 4-Anilino-7-trifluoromethylquinazoline

HRID 358031

Reaction equation

HRID 358031 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.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[NH:16]([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)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 128067424-Chloro-7-(trifluoromethyl)quinazoline

Product 1

HCID 128067734-Anilino-7-trifluoromethylquinazolineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of 4-chloro-7-trifluoromethylquinazoline were dissolved in 10 ml of ethanol, and 1.0 g of aniline was added to the solution. Reaction occurred violently and the reaction mixture solidified immediately. After cooling, the solidified product was collected and washed with ethanol. The resulting crystals were pulverized and added to a dilute aqueous solution of sodium hydroxide. Insolubles were filtered off and recrystallized from ethanol to give 1.7 g (yield 60%) of the desired Compound No. 17 in the form of colourless plates melting at 230°-232° C.

Workup

  1. customReaction
  2. temperatureAfter cooling
  3. customthe solidified product was collected
  4. washwashed with ethanol
  5. additionadded to a dilute aqueous solution of sodium hydroxide
  6. filtrationInsolubles were filtered off
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-286f2e10af6c4eb48b67a76a2bfad034
Source dataset
uspto-grants-1984_08
Patent number
US04464375

Linked notes

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