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

HRID 1165788Notes

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

Conditions

Temperature: 5 °C

Procedure

Triethylamine (16.2 cc) is added with stirring, to a solution of D series 10-[1-hydroxy-2-propyl)phenothiazinecarbonitrile (20 g) in methylene chloride (200 cc) cooled to a temperature of about 5° C., then a solution of methanesulphonyl chloride (8.9 cc) in methylene chloride (89 cc) is poured in dropwise over 25 minutes, and stirring is continued for 50 minutes at a temperature of about 10° C. The reaction mixture is washed successively with distilled water (2×00 cc) and a saturated aqueous solution of sodium chloride (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. D series 2-(2-cyano-10-phenothiazinyl)-1-propyl methanesulphonate (25.8 g) is thus obtained in the form of an orange gum which is used without other purification for the syntheses following.

Workup

washThe reaction mixture is washed successively with distilled water (2×00 cc)
dry with materiala saturated aqueous solution of sodium chloride (100 cc), dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record: ord-e39d175e83004c33b389f9230154c2e2
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04912105

Reaction notes

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