Water → HCID 18965314, 화합물

HRID 2226738노트

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HRID 2226738 반응식
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl.O>C(OCCCC)CCC.ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

참가 물질

7

반응물 4

HCID 962WaterHCID 7108PhenothiazineHCID 24758Sodium hydrideHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxane

생성물 1

HCID 18965314HCID 18965314, 화합물수율 55.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8909Butyl ether용매

반응 조건

온도
135 °C

실험 절차

Phenothiazine (3.8 g, 19 mmol) was added to a suspension of sodium hydride (0.92 g, 23 mmol, 60% oil dispersion) in dry dibutylether (25 ml) under an atmosphere of nitrogen. The mixture was heated at 135° C. for 1 h and then cooled to approximately 100° C. 2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethylchloride (8 g, 38 mmol) was added in one portion and the mixture was heated overnight at 110° C. The reaction mixture was poured into water (250 ml) and extracted with dichloromethane (3×50 ml) and diethyl ether (50 ml). The combined organic extracts were washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo leaving an oil, which was submitted to column chromatography using dichloromethane as eluent. Collecting the proper fractions afforded 3.9 g of crude 10-(2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethyl)-10H-phenothiazine. TLC: rf=0.72 (SiO2 ; dichloromethane/methanol=19:1).

후처리

  1. temperaturecooled to approximately 100° C
  2. temperaturethe mixture was heated overnight at 110° C
  3. extractionextracted with dichloromethane (3×50 ml) and diethyl ether (50 ml)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was evaporated in vacuo
  7. customleaving an oil, which
  8. customCollecting the proper fractions

출처 및 근거

ORD 기록
ord-d6041f89af2f4048ba1c3adb14d74cf5
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348965

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