Phosphorus oxychloride → 1-Chloro-4-(4-methoxybenzyl)phthalazine

HRID 593935노트

반응식

HRID 593935 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=O)[NH:10][N:9]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:23])=O>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([Cl:23])=[N:10][N:9]=2)=[CH:5][CH:4]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 123328504-(4-methoxybenzyl)phthalazin-1(2H)-one

생성물 1

HCID 866141621-Chloro-4-(4-methoxybenzyl)phthalazine

실험 절차

To 4-(4-methoxybenzyl)phthalazin-1(2H)-one (1.18 g, 4.43 mmol) was added phosphorus oxychloride (4.13 ml, 44.3 mmol). A water condenser was attached and the mixture was heated to reflux under a nitrogen atmosphere for 15 hours. The reaction was concentrated in vacuo, diluted with methylene chloride and ice water, then quenched with solid sodium bicarbonate until pH was basic and gas evolution ceased. The layers were separated and the organic layers were dried over sodium sulfate, filtered through a pad of silica gel using EtOAc and concentrated to yield 1-(4-methoxybenzyl)-4-chlorophthalazine as a light orange solid. MS m/z=285 [M+1]+. Calc'd for C16H13ClN2O: 284.75.

후처리

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere for 15 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. additiondiluted with methylene chloride and ice water
  6. customquenched with solid sodium bicarbonate until pH
  7. customThe layers were separated
  8. dry with materialthe organic layers were dried over sodium sulfate
  9. filtrationfiltered through a pad of silica gel
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8846e630b1e444c5988999cdbb33632b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242961B2

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