4-Toluenesulfonyl chloride → HCID 86672634, compound

HRID 2369312Notes

Reaction equation

HRID 2369312 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]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:26][CH2:27][CH2:28][OH:29].CN(C)CCCN>C(Cl)Cl.C(OCC)(=O)C>[CH3:24][C:25]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])=[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 86672633HCID 86672633, compound

Product 1

HCID 86672634HCID 86672634, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.63 mL (4.6 mmol) of triethylamine, 0.87 g (4.6 mmol) of p-toluenesulfonyl chloride, and 20 mg (0.21 mmol) of trimethylamine hydrochloride were added to a solution of 1.0 g (4.2 mmol) of 4,8,12-trimethyltridec-3-en-1-ol in dry methylene chloride (3 mL) at 0° C., sequentially. After being stirred for 2 hours at room temperature, 0.10 mL (0.83 mmol) of N,N-dimethyl-1,3-propanediamine was added to the reaction mixture at 0° C. After being stirred for 30 min, the mixture was diluted with ethyl acetate. The resulting solution was washed with water, 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-trimethyltridec-3-enyl)tosylate as a crude product.

Workup

  1. stirringAfter being stirred for 30 min
  2. washThe resulting solution was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  3. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dde91abc788744e287aceed227cc6a04
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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