Sodium Hydroxide → HCID 86743540, compound

HRID 476545Notes

Reaction equation

HRID 476545 reaction equation
[OH-].[Na+].O.[C:4]1([CH3:14])[CH:9]=[CH:8][C:7]([S:10]([OH:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Cl-].[CH2:16]([N+:34]([CH3:43])([CH3:42])[CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][C:37]1=[O:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O>[S:10]([C:7]1[CH:8]=[CH:9][C:4]([CH3:14])=[CH:5][CH:6]=1)([O-:13])(=[O:12])=[O:11].[CH2:16]([N+:34]([CH3:43])([CH3:42])[CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][C:37]1=[O:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 14093935HCID 14093935, compound

Product 1

HCID 86743540HCID 86743540, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask equipped with stirrer and thermometer was added at ambient temperature 50.0 g. distilled water 7.2 g. sodium hydroxide solution (50%) and 13.3 g. (0.069 m) p-toluenesulfonic acid monohydrate, [C6H4 (CH3)-SO3H]. The mixture was stirred at ambient temperature for about 0.5 hour, after which 30.0 g. (0.069 m) octadecyldimethyl N-[(2-pyrrolidonyl) methyl]ammonium chloride was added. The reaction mixture was heated to 40°-45° to ensure complete solution and stirring continued for an additional 2 hours. The reaction was then cooled to 10°-15° C. to precipitate the crude tosylate salt product. The crude product was filtered to recover 19.8 g. of white solid product, which product was found to have 98.2% quaternized product, 0.4% amine, and 0.04% chloride. The above solid was heated in a 50° oven for 30 days and showed no loss of activity.

Workup

  1. customTo a flask equipped with stirrer
  2. additionthermometer was added at ambient temperature 50.0 g
  3. temperatureThe reaction mixture was heated to 40°-45°
  4. stirringstirring
  5. waitcontinued for an additional 2 hours
  6. temperatureThe reaction was then cooled to 10°-15° C.
  7. customto precipitate the crude tosylate salt product
  8. filtrationThe crude product was filtered
  9. customto recover 19.8 g
  10. temperatureThe above solid was heated in a 50° oven for 30 days

Sources & evidence

ORD record
ord-0d9a1979143e46eb9b1ebcd7a0884efe
Source dataset
uspto-grants-1989_12
Patent number
US04885158

Reaction notes

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