Triethylamine → 2-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamide

HRID 2388660Notes

Reaction equation

HRID 2388660 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[S:23](Cl)(=[O:25])=[O:24]>ClCCl>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[S:23]([N:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:5][CH2:6][OH:7])(=[O:24])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chlorideHCID 191005662-(Cyclopropylamino)ethan-1-ol

Product 1

HCID 579162662-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 2-(cyclopropylamino)ethanol (2 eq.) was added triethylamine (2.5 eq.) and the mixture was cooled to 0° C. To this cold reaction mixture was added 2-chloro-6-methylbenzene sulfonyl chloride (1 eq.) and the mixture was stirred at 25° C. for 2 h. It was diluted with dichloromethane and the organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of the organic layer under reduced pressure gave the crude product which was purified by column chromatography (10% ethyl acetate in hexane). Yield: 50%

Workup

  1. customTo this cold reaction mixture
  2. washthe organic layer was washed with water and brine
  3. dry with materialfinally dried over sodium sulfate
  4. customEvaporation of the organic layer under reduced pressure

Sources & evidence

ORD record
ord-957ed86906ed4f3287e08ef0fe300a86
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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