Water → HCID 20478815, compound

HRID 1105757Notes

Reaction equation

HRID 1105757 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:5])=[O:4].[F:15][C:16]([F:20])=[C:17]([F:19])[F:18].[OH-].[K+].O>CN(C)C=O>[CH3:1][N:2]([C:17]([F:19])([F:18])[CH:16]([F:20])[F:15])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8301TetrafluoroethyleneHCID 14797Potassium HydroxideHCID 264906N-methyl-2-nitrobenzene-1-sulfonamide

Product 1

HCID 20478815HCID 20478815, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 72 g of N-methyl-2-nitrobenzenesulfonamide, 35 g of tetrafluoroethylene and 4 g of powdered potassium hydroxide in 150 ml of dimethylformamide was heated at 85° for 3 hours in a pressure vessel. The reaction mixture was cooled to 25° and poured into 800 ml of water. A heavy oil was separated and the aqueous layer extracted with 150 ml of 1-chlorobutane. The heavy oil, the 1-chlorobutane extract and an additional 300 ml of 1-chlorobutane were combined and washed three times with water. The organic solution was dried over magnesium sulfate and concentrated in-vacuo to yield 85.1 g of N-methyl-N-(1,1,2,2-tetrafluoroethyl)-2-nitrobenzenesulfonamide as a viscous orange oil.

Workup

  1. temperatureThe reaction mixture was cooled to 25°
  2. customA heavy oil was separated
  3. extractionthe aqueous layer extracted with 150 ml of 1-chlorobutane
  4. extractionThe heavy oil, the 1-chlorobutane extract
  5. washwashed three times with water
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-8d617229b78d48edaf5c452eb5f7337b
Source dataset
uspto-grants-1982_01
Patent number
US04310346

Reaction notes

Loading…