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Water → (2RS)-2-(7-chloro-2-cyano-10-phenothiazinyl)propyl methanesulphonate

HRID 704225
ノート
印刷プレビュー

反応式

HRID 704225 の反応式
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH:23]([CH3:26])[CH2:24][OH:25])[C:18]1[CH:17]=[C:16]([C:27]#[N:28])[CH:15]=[CH:14][C:13]=1[S:12]2.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>C(Cl)Cl>[CH3:29][S:30]([O:25][CH2:24][CH:23]([N:19]1[C:18]2[CH:17]=[C:16]([C:27]#[N:28])[CH:15]=[CH:14][C:13]=2[S:12][C:11]2[C:20]1=[CH:21][CH:22]=[C:9]([Cl:8])[CH:10]=2)[CH3:26])(=[O:32])=[O:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 159253677-chloro-10-[(2RS)-1-hydroxy-2-propyl]-2-phenothiazinecarbonitrile

生成物 1

HCID 15925250(2RS)-2-(7-chloro-2-cyano-10-phenothiazinyl)propyl methanesulphonate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

Triethylamine (30 cc) is added to a solution of 7-chloro-10-[(2RS)-1-hydroxy-2-propyl]-2-phenothiazinecarbonitrile (40 g) in methylene chloride (400 cc). The mixture is cooled to 0° C. and then treated dropwise in the course of 1 hour with methanesulphonyl chloride (16.6 cc). Distilled water (1 liter) is then added, after which the constituents of the mixture are allowed to settle and the organic phase is separated and washed with distilled water (500 cc). The organic phase is then dried over magnesium sulphate, filtered and concentrated under reduced pressure (30 mm Hg; 4 kPa) to a residual volume of 100 cc. Isopropyl ether (150 cc) is then introduced slowly and the mixture is left stirred for 30 minutes. Isopropyl ether (300 cc) is then added slowly and the suspension is stirred for 48 hours. The precipitate is filtered off, washed with isopropyl ether (2×50 cc) and dried at 40° C. under reduced pressure (5 mm Hg; 0.67 kPa) to give (2RS)-2-(7-chloro-2-cyano-10-phenothiazinyl)propyl methanesulphonate (34.53 g), m.p. 132° C.

後処理

  1. customthe organic phase is separated
  2. washwashed with distilled water (500 cc)
  3. dry with materialThe organic phase is then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa) to a residual volume of 100 cc
  6. additionIsopropyl ether (150 cc) is then introduced slowly
  7. waitthe mixture is left
  8. additionIsopropyl ether (300 cc) is then added slowly
  9. stirringthe suspension is stirred for 48 hours
  10. filtrationThe precipitate is filtered off
  11. washwashed with isopropyl ether (2×50 cc)
  12. customdried at 40° C. under reduced pressure (5 mm Hg; 0.67 kPa)

出典と根拠

ORDレコード
ord-86e05c2815c14a46aec0bf94ede06c9e
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04985419

反応ノート

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