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Phosphorus oxychloride → 10-Ethylphenothiazine-3-carbaldehyde

HRID 355417
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HRID 355417 반응식
CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH2:16]([N:18]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[S:25][C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17].C([O-])(=O)C.[Na+]>ClC1C=CC=CC=1Cl>[CH2:16]([N:18]1[C:19]2[CH:20]=[CH:21][C:22]([CH:9]=[O:10])=[CH:23][C:24]=2[S:25][C:26]2[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 219178N-EthylphenothiazineHCID 517045Sodium Acetate

생성물 1

HCID 31433010-Ethylphenothiazine-3-carbaldehyde수율 69%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
100 °C

실험 절차

N-Methylformanilide (5.35 ml, 43.6 mmol) and phosphorus oxychloride (4.06 ml, 43.6 mmol) were added at room temperature to a mixture of 10-ethylphenothiazine (7.62 g, 33.5 mmol) and 1,2-dichlorobenzene (34 ml), and the mixture was stirred at 100° C. for 24 hours. At room temperature, a sodium acetate aqueous solution (45 wt. %, 85 g) was added to the reaction mixture, which was subsequently concentrated under a reduced pressure. Ethyl acetate and water (each 300 ml) were added to the resulting residue in that order and then the reaction product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to give the title compound (5.91 g, 23.1 mmol, 69%) as yellow crystals.

후처리

  1. concentrationwas subsequently concentrated under a reduced pressure
  2. additionEthyl acetate and water (each 300 ml) were added to the resulting residue in that order
  3. extractionthe reaction product was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-1437272821134a61a16b6222de15954f
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05830902

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