Sodium Chloride → HCID 67827129, compound

HRID 1109532Notes

Reaction equation

HRID 1109532 reaction equation
[Cl-:1].[Na+].COS([O-])(=O)=O.[CH3:9][N+:10]1([CH2:15][CH:16]([N:18]2[C:31]3[CH:30]=[C:29]([C:32](=[O:37])[NH:33][CH2:34][CH2:35][CH3:36])[CH:28]=[CH:27][C:26]=3[S:25][C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11]1>O.C(#N)C.C(OCC)C>[Cl-:1].[CH3:9][N+:10]1([CH2:15][CH:16]([N:18]2[C:31]3[CH:30]=[C:29]([C:32](=[O:37])[NH:33][CH2:34][CH2:35][CH3:36])[CH:28]=[CH:27][C:26]=3[S:25][C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 5234Sodium ChlorideHCID 19020528HCID 19020528, compound

Product 1

HCID 67827129HCID 67827129, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A saturated aqueous sodium chloride solution (35 cc) is added in the course of 10 minutes with stirring at 20° C. to a solution of 1-methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium methylsulphate, L series (6.15 g), in distilled water (10 cc). The oil formed is then allowed to settle, the mixture is cooled to a temperature in the region of 0° C. for 90 minutes and the supernatant is thereafter removed. The yellow oil is taken up in distilled water (3.5 cc) and saturated aqueous sodium chloride solution (17 cc) is added. The emulsion formed is separated after settling has taken place and cooled for 2 hours to a temperature in the region of 0° C., and the supernatant is removed. The yellow oil formed is dissolved in acetonitrile (80 cc) and the solution is dried 3 times over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) under a dry atmosphere at 50° C. The yellow meringue-like residue thereby obtained (4.52 g) is subjected to an azeotropic distillation in solution in 1,2-dichloroethane (80 cc) in order to remove the final traces of water, and the solution is then concentrated to dryness under reduced pressure (5 mm Hg; 0.7 kPA) at 20° C. under a dry atmosphere. The yellowish meringue-like residue thereby obtained (5 g) is stirred for 2 hours in suspension in anhydrous diethyl ether (100 cc), filtered, washed with diethyl ether (2×5 cc), drained and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C. 1-Methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium chloride, L series (4.5 g), is thereby obtained in the form of an amorphous white solid, m.p. about 240° C., the infrared spectrum of which is identical to that of the product of Example 4.

Workup

  1. customThe oil formed
  2. customthe supernatant is thereafter removed
  3. additionsaturated aqueous sodium chloride solution (17 cc) is added
  4. customThe emulsion formed
  5. customis separated after settling
  6. temperaturecooled for 2 hours to a temperature in the region of 0° C.
  7. customthe supernatant is removed
  8. customThe yellow oil formed
  9. dry with materialthe solution is dried 3 times over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) under a dry atmosphere at 50° C
  12. customThe yellow meringue-like residue thereby obtained (4.52 g)
  13. distillationis subjected to an azeotropic distillation in solution in 1,2-dichloroethane (80 cc) in order
  14. customto remove the final traces of water
  15. concentrationthe solution is then concentrated to dryness under reduced pressure (5 mm Hg; 0.7 kPA) at 20° C. under a dry atmosphere
  16. customThe yellowish meringue-like residue thereby obtained (5 g)
  17. filtrationfiltered
  18. washwashed with diethyl ether (2×5 cc)
  19. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C

Sources & evidence

ORD record
ord-c00c60d4f54241a9862d6146c4c36d28
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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