Chloranil → 6-Nitro-2-(1,3-benzodioxole-5-yl)-quinazoline

HRID 217137

반응식

HRID 217137 반응식
Cl.[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([NH2:13])=[C:9]([CH:12]=1)[CH2:10][NH2:11])([O-:4])=[O:3].[C:14](Cl)(=O)[C:15]1[CH:23]=[CH:22][C:21]2[O:20][CH2:19][O:18][C:17]=2[CH:16]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[N+:2]([C:5]1[CH:12]=[C:9]2[C:8](=[CH:7][CH:6]=1)[N:13]=[C:14]([C:15]1[CH:23]=[CH:22][C:21]3[O:20][CH2:19][O:18][C:17]=3[CH:16]=1)[N:11]=[CH:10]2)([O-:4])=[O:3]

참가 물질

6

반응물 3

HCID 8371ChloranilHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 230857072-(Aminomethyl)-4-nitroaniline hydrochloride

생성물 1

HCID 578631566-Nitro-2-(1,3-benzodioxole-5-yl)-quinazoline수율 82.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 5-nitro-2-amino-benzylamine hydrochloride (31 g, 0.152 mol) in DCM (450 ml) was added at 0° C. TEA (52.6 ml, 0.38 mol) and a solution of piperonyloyl chloride (27.3 g, 0.16 mol) in DCM (80 ml). The mixture was stirred for 2 hours at r.t. The solvent was removed i.v. and the residue triturated with ethanol/water 1/9, then with diisopropyl ether. The obtained solid was dried and suspended in toluene (900 ml) and POCl3 (670 ml). The mixture was heated at reflux for 2 hours, then the solvent was removed i.v. and the residue was triturated with water/ammonia, washed with water, dried over P2O5. A mixture of the obtained product and chloranil (32.7 g, 0.129 mol) in toluene (500 ml) was heated at reflux for 2 hours. The mixture was concentrated i.v. and the residue was triturated with NaOH 1M, washed with water and with methanol. The obtained solid was dried i.v. (37 g, 82.5% yield). C15H9N3O4, MW: 295.26, mp 220-222° C.

후처리

  1. additionwas added at 0° C
  2. customThe solvent was removed i.v
  3. customand the residue triturated with ethanol/water 1/9
  4. customThe obtained solid was dried
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 2 hours
  7. customthe solvent was removed i.v
  8. customand the residue was triturated with water/ammonia
  9. washwashed with water
  10. dry with materialdried over P2O5
  11. temperaturewas heated
  12. temperatureat reflux for 2 hours
  13. concentrationThe mixture was concentrated i.v
  14. customand the residue was triturated with NaOH 1M
  15. washwashed with water and with methanol
  16. customThe obtained solid was dried i.v

출처 및 근거

ORD 기록
ord-808266bd50b44deb9e23ca3d7e66ac90
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193353B2

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