Triethylamine → 4-Allylamino-2-(2,2,2-trifluoroethylamino)-6-nitroquinazoline

HRID 1250607Notes

Reaction equation

HRID 1250607 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7](Cl)[N:6]=1)[CH:2]=[CH2:3].[F:19][C:20]([F:24])([F:23])[CH2:21][NH2:22].C(N(CC)CC)C>>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:22][CH2:21][C:20]([F:24])([F:23])[F:19])[N:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 183265624-Allylamino-2-(2,2,2-trifluoroethylamino)-6-nitroquinazolineYield 30.8%

Procedure

A mixture of 150 mg (0.57 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline, 772 mg (5.70 mmol) of 2,2,2-trifluoroethylamine and 1.15 g (11.4 mmol) of triethylamine was stirred in a sealed tube at room temperature for 16 hours. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with chloroform (10 ml×3). After the organic layer was washed with brine and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography to give 57 mg (yield: 30.8%) of the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction with chloroform (10 ml×3)
  3. washAfter the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-755905076abf4007b5bf965e0139a8f0
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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