Acetonitrile → HCID 86639521, compound

HRID 1022397Notes

Reaction equation

HRID 1022397 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.C(#N)C.Cl.[CH3:23][O:24][NH2:25].C(N(CC)CC)C>O>[Cl:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:25][O:24][CH3:23])[N:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 16282212,6-dichloro-4-phenylquinazoline

Product 1

HCID 86639521HCID 86639521, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 275 mg of 2,6-dichloro-4-phenylquinazoline (compound No. Ia1-3), 10 ml of acetonitrile and 334 mg of methoxyamine hydrochloride was added dropwise 506 mg of triethylamine at room temperature to obtain a mixture. The mixture was charged in a pressure-resistant reaction vessel made of stainless steel and the reaction was carried out at 105° C. for 3.5 hours. After cooling, the reaction solution was poured into 100 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 purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 156 mg of crude crystals. The crude crystals were recrystallized from ethyl acetate to obtain 55 mg of the titled compound. Mp.173.9° C. 1H NMR (CDCl3): 3.98 (3H, s), 7.47-7.72 (6H, m), 7.87 (1H, d, J=9.0 Hz), 7.89 (1H, d, J=2.2 Hz), 8.03 (1H, br. s).

Workup

  1. customto obtain a mixture
  2. additionThe mixture was charged in a pressure-resistant reaction vessel
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. extractionthe resultant extract
  6. washwas washed with water
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  9. customto obtain 156 mg of crude crystals
  10. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b4cda63bc41d4228991113abf29b0927
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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