Water → N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine

HRID 893881Notes

Reaction equation

HRID 893881 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[CH:11]([S:13]([F:16])(=[O:15])=[O:14])=[CH2:12].O>C(O)(C)C>[F:16][S:13]([CH2:11][CH2:12][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 7603N-ethyl-3-methylanilineHCID 69612Ethenesulfonyl fluoride

Product 1

HCID 21161675N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-Ethyl-m-toluidine (66.5 g) (0.05 m) is dissolved in isopropyl alcohol (75 ml) and vinylsulfonyl fluoride (55 g 0.5) is added dropwise over 1.25 hr. The reaction exotherms to 38° C. and the reaction mixture is stirred for 1 hr. at ambient temperature and drowned into 500 ml of ice and water. The product is collected by filtration, washed with water, and dried in air. The product melts at 32°-34° C.

Workup

  1. customexotherms to 38° C.
  2. customat ambient temperature
  3. filtrationThe product is collected by filtration
  4. washwashed with water
  5. customdried in air

Sources & evidence

ORD record
ord-4b7f339d34494919a1882e2afbf93a28
Source dataset
uspto-grants-1981_08
Patent number
US04282144

Reaction notes

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