Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 639964노트

반응식

HRID 639964 반응식
CN(C)C=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[NH:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)([Cl:27])=O>>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([Cl:27])=[N:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

생성물 1

HCID 220309237-(Benzyloxy)-4-chloroquinazoline수율 86.5%

실험 절차

Dimethylformamide (0.5 ml) was added to a suspension of 7-(benzyloxy)quinazolin-4-(3H)-one (5.04 g, 20 mmol) in thionyl chloride (50 ml) and the mixture heated at reflux for 2 hours. The thionyl chloride was removed in vacuo and the residual oil dissolved in dichloromethane (100 ml). This solution was slowly added to an aqueous saturated solution of sodium bicarbonate (100 ml) and the organic phase recovered. The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined organics dried and concentrated to yield 7-(benzyloxy)-4-chloroquinazoline (4.68 g, 86.5% yield):

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customThe thionyl chloride was removed in vacuo
  4. dissolutionthe residual oil dissolved in dichloromethane (100 ml)
  5. additionThis solution was slowly added to an aqueous saturated solution of sodium bicarbonate (100 ml)
  6. customthe organic phase recovered
  7. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
  8. customthe combined organics dried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4698f4b36e6e4f409dbeecfcb95d0a52
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691867B2

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