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

HRID 728704Notes

Reaction equation

HRID 728704 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26]#[N:27])[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:26]#[N:27])[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 14502136HCID 14502136, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (10 cc) is added with stirring to a solution, cooled to a temperature in the region of 5° C., of 10-(1-hydroxy-2-propyl)-2-phenothiazinecarbonitrile, L series (12.6 g) in methylene chloride (126 cc), a solution of methanesulphonyl chloride (5.6 cc) in methylene chloride (56 cc) is then added dropwise during 25 minutes, and stirring is continued for 1 hour 15 minutes at a temperature in the region of 10-15° C. The reaction mixture is washed successively with distilled water (2×100 cc) and with saturated 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, L series (16.2 g) is thereby obtained in the form of an orange oil.([α]20D =+29.9±0.3°; 2.4%; chloroform), 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 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-d256e377c4d34d1db59c56f160e5491a
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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