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Methanesulfonic Acid → Distearyl Dimethyl Ammonium Methyl Sulfonate

HRID 1196450
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HRID 1196450 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6395Methanesulfonic Acid2회HCID 77450Dimethyldioctadecylammonium methyl sulfateHCID 44516822Dabrafenib Mesylate

생성물 1

HCID 15031834Distearyl Dimethyl Ammonium Methyl Sulfonate

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-70aabc56f31a42368ba7b3d13022e467
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05114821

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