Water → 4-Toluenesulfonyl chloride

HRID 611058Notes

Reaction equation

HRID 611058 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:13]=[CH:12][O:11][CH:10]=1)[CH2:5][CH2:6]O)[CH:2]=[CH2:3].C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([Cl:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([N:4]([CH2:5][CH2:6][Cl:30])[CH2:8][C:9]1[CH:13]=[CH:12][O:11][CH:10]=1)[CH:2]=[CH2:3].[C:21]1([CH3:31])[CH:22]=[CH:23][C:24]([S:27]([Cl:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19599884HCID 19599884, compound

Product 2

HCID 73974-Toluenesulfonyl chlorideHCID 19600271HCID 19600271, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.255 g (51.07 mmol) of the above 2-[allyl-(3-furylmethyl)amino]ethanol, 10.7 ml (76.6 mmol) of triethylamine and 0.1 g of 4-dimethylaminopyridine in 150 ml of dichloromethane, 11.7 g (61.3 mmol) of p-toluenesulfonyl chloride was added at room temperature, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield N-allyl-N-(3-furylmethyl)-2-chloroethylamine as a mixture with p-toluenesulfonyl chloride.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

Sources & evidence

ORD record
ord-d3f9e59d814341e78a808f8b808f137f
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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