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

HRID 704225Notes

Reaction equation

HRID 704225 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-86e05c2815c14a46aec0bf94ede06c9e
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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