Water → HCID 18965314、化合物

HRID 2226738ノート

反応式

HRID 2226738 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 18965314HCID 18965314、化合物収率 55.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8909Butyl ether溶媒

反応条件

温度
135 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d6041f89af2f4048ba1c3adb14d74cf5
出典データセット
uspto-grants-1994_09
特許番号
US05348965

反応ノート

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