Methanesulfonic Acid → Distearyl Dimethyl Ammonium Methyl Sulfonate

HRID 1196450Notes

Reaction equation

HRID 1196450 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].COS([O-])(=O)=O.[CH2:12]([N+:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])([CH3:32])[CH3:31])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CC(C1SC(C2C=CN=C(N)N=2)=C(C2C=CC=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=2F)N=1)(C)C.CS(O)(=O)=O>O>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH2:33]([N+:30]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH3:32])[CH3:31])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

5

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 77450Dimethyldioctadecylammonium methyl sulfateHCID 44516822Dabrafenib Mesylate

Product 1

HCID 15031834Distearyl Dimethyl Ammonium Methyl Sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 500 milliliters of water was added 54 milliliters (80 grams, 0.83 mol, 3.7 eq.) of methane sulfonic acid, CH3SO3H (available from Aldrich Chemical Compoany or Eastman Kodak Company). This solution, when cooled to room temperature, was added to a suspension of distearyl dimethyl ammonium methyl sulfate (DDAMS) (150.0 grams, 0.227 mol) suspended in 600 milliliters of water. The mixture was heated (70° to 80° C.) on a hot plate with stirring for 4 hours, cooled to room temperature and allowed to stand overnight. The mixture separated into an off-white/tan solid layer atop an aqueous layer. The mixture was filtered under reduced pressure and washed with water and air dried. The crude material was recrystallized from acetone and small amounts of methylene chloride. The methylene chloride appeared to help remove an unidentified waxy/sticky impurity to afford: 110 grams (0.17 mol), m.p. 70° C. (softening), 90° C. (liquid), and a second crop 13.7 grams (0.021 mol), m.p. 70° C. (softening), 87° C. (liquid) of the desired methane sulfonate salt (DDAMES).

Workup

  1. temperatureThe mixture was heated (70° to 80° C.) on a hot plate
  2. temperaturecooled to room temperature
  3. waitto stand overnight
  4. customThe mixture separated into an off-white/tan solid layer atop an aqueous layer
  5. filtrationThe mixture was filtered under reduced pressure
  6. washwashed with water and air
  7. customdried
  8. customThe crude material was recrystallized from acetone and small amounts of methylene chloride
  9. customto help remove an unidentified waxy/sticky impurity
  10. customto afford
  11. custom110 grams (0.17 mol), m.p. 70° C. (softening), 90° C. (liquid)

Sources & evidence

ORD record
ord-70aabc56f31a42368ba7b3d13022e467
Source dataset
uspto-grants-1992_05
Patent number
US05114821

Reaction notes

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