Benzylamine → 2-Chloro-4-benzylamino-6-nitroquinazoline

HRID 1250564Notes

Reaction equation

HRID 1250564 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[Cl:18][C:9]1[N:8]=[C:7]([NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 183265332-Chloro-4-benzylamino-6-nitroquinazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 367 mg (1.77 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 15.13 g (98.70 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 379 mg (3.54 mmol) of benzylamine under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, and crystals thus precipitated were filtered out to obtain 2-chloro-4-benzylamino-6-nitroquinazoline. To this was added 761 mg (13.33 mmol) of allylamine, and the resulting mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 224 mg (yield: 56.8%) of the title compound.

Workup

  1. customreaction in the same manner as in Example 10
  2. customthus precipitated
  3. filtrationwere filtered out

Sources & evidence

ORD record
ord-141652116b1644c7a1ce2bea9d19db00
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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