Triethylamine → 2-(2-Cyano-10-phenothiazinyl)propyl mesylate

HRID 704198Notes

Reaction equation

HRID 704198 reaction equation
C([N:3]([CH2:6]C)CC)C.[OH:8][CH2:9][CH:10]([N:12]1[C:25]2[C:24](C#N)=[CH:23][CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([O:8][CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:6]#[N:3])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54062112HCID 54062112, compound

Product 1

HCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (16.2 cc) is added with stirring to a solution, cooled to a temperature in the region of 5° C., of 10-(1-hydroxy-2-propyl)phenothiazinecarbonitrile, D series (20 g) in methylene chloride (200 cc), a solution of methanesulphonyl chloride (8.9 cc) in methylene chloride (89 cc) is then introduced dropwise during 25 minutes, and stirring is continued for 50 minutes at a temperature in the region of 10° C. The reaction mixture is washed successively with distilled water (2×100 cc) and with saturated aqueous sodium chloride solution (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 2-(2-Cyano-10-phenothiazinyl)-1-propyl methanesulphonate, D series (25.8 g) is thereby obtained in the form of an orange gum, which is used without further purification for the next stage of the synthesis.

Workup

  1. stirringstirring
  2. washThe reaction mixture is washed successively with distilled water (2×100 cc) and with saturated aqueous sodium chloride solution (100 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-b7fb2fbd6e104bf3be45e8be09e1587c
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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