4-Toluenesulfonyl chloride → HCID 86672628, compound

HRID 2369287Notes

Reaction equation

HRID 2369287 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl.CN(C)C.[CH3:24][C:25]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:26][CH2:27][CH2:28][OH:29].CN(C)CCCN>C(Cl)Cl.O>[CH3:24][C:25]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:26][CH2:27][CH2:28][O:29][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

8

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 86672627HCID 86672627, compound

Product 1

HCID 86672628HCID 86672628, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 0.49 mL (3.5 mmol) of triethylamine, 0.68 g (3.54 mmol) of p-toluenesulfonyl chloride, and 15 mg (0.16 mmol) of trimethylamine hydrochloride were added to a solution of 1.0 g (3.2 mmol) of 4,8,12,16-tetramethylheptadec-3-en-1-ol in dry methylene chloride (3.2 mL) at 0° C., sequentially. After being stirred for 2 hours at room temperature, 0.080 mL (0.64 mmol) of N,N-dimethyl-1,3-propanediamine was added to the reaction mixture at 0° C. After being stirred for 15 min, water was added, and the mixture was extracted with methylene chloride. The extract was washed with 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain (4,8,12,16-tetramethylheptadec-3-enyl)tosylate as a crude product.

Workup

  1. stirringAfter being stirred for 15 min
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe extract was washed with 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  4. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-97d0a0528dc843b2bd1cf9fdba3b03ed
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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