Furfurylamine → HCID 9291888, compound

HRID 1022408Notes

Reaction equation

HRID 1022408 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.[CH2:19]([NH2:25])[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1>O>[Cl:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:25][CH2:19][C:20]1[O:24][CH:23]=[CH:22][CH:21]=1)[N:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 16282212,6-dichloro-4-phenylquinazoline

Product 1

HCID 9291888HCID 9291888, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 275 mg of 2,6-dichloro-4-phenylquinazoline (compound No. II-2) and 486 mg of furfurylamine was stirred at 85° C. for 40 minutes and then poured into 50 ml of water. The mixture was extracted with ethyl acetate, and the resultant extract was washed with water and then concentrated. The resulting residue was recrystallized from ethanol to obtain 280 mg of the titled compound. Mp.142.0° C. 1H NMR (CDCl3): 4.77 (2H, d, J=5.6 Hz), 5.70 (1H, br. t, J=5.6 Hz), 6.29-6.32 (2H, m), 7.36 (1H, dd, J=1.8, 0.9 Hz), 7.53-7.70 (7H, m), 7.78 (1H, d, J=2.2 Hz).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe resultant extract
  3. washwas washed with water
  4. concentrationconcentrated
  5. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a9eb6adb92564a628e189e39bb4a4f35
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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