Dimethylformamide → 4,7-Dichloro-6-nitroquinazoline

HRID 1838539

반응식

HRID 1838539 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].P(Cl)(Cl)([Cl:18])=O.CN(C=O)C>S(Cl)(Cl)=O>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=2)[N:9]=[CH:8][N:7]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1356875047-Chloro-6-nitroquinazolin-4(1H)-one

생성물 1

HCID 104904554,7-Dichloro-6-nitroquinazoline수율 81%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

A mixture of 7-chloro-6-nitro-3,4-dihydroquinazolin-4-one (40 g, 0.18 mol), (J. Org. Chem. 1975, 40, 356), phosphorus oxychloride (50 ml) and DMF (1 ml) in thionyl chloride (300 ml) was heated at reflux for 4 hours. The reaction mixture was allowed to cool and the volatiles removed by evaporation and by azeotroping with toluene. The residue was basified with aqueous sodium hydrogen carbonate solution and extracted with methylene chloride (4×100 ml). The extracts were combined, washed with brine and filtered through phase separating paper. The solvent was removed by evaporation and the residue triturated with ether/isohexane to give 4,7-dichloro-6-nitroquinazoline (35.2 g, 81%) as a pale yellow solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. customthe volatiles removed by evaporation
  5. customby azeotroping with toluene
  6. extractionextracted with methylene chloride (4×100 ml)
  7. washwashed with brine
  8. filtrationfiltered through phase
  9. customseparating paper
  10. customThe solvent was removed by evaporation
  11. customthe residue triturated with ether/isohexane

출처 및 근거

ORD 기록
ord-9337bab50e5f4d94846c3b598158b530
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673803B2

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