Water → HCID 86741353, compound

HRID 1906384Notes

Reaction equation

HRID 1906384 reaction equation
[CH3:1][C:2]([NH:6][S:7]([CH:10]=[CH2:11])(=[O:9])=[O:8])([CH3:5])[C:3]#[N:4].[Cl:12][C:13]([Cl:19])([S:17]Cl)[CH:14]([Cl:16])[Cl:15].O.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Cl:12][C:13]([S:17][CH2:5][C:2]([CH3:1])([NH:6][S:7]([CH:10]=[CH2:11])(=[O:9])=[O:8])[C:3]#[N:4])([Cl:19])[CH:14]([Cl:16])[Cl:15]

Participants

7

Reactant 4

HCID 962WaterHCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14798Sodium HydroxideHCID 13799778HCID 13799778, compound2×

Product 1

HCID 86741353HCID 86741353, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3.9 g (0.02 mole) 2-methyl-2-(ethenylsulfonamido)propionitrile (the product of Example 22), 5.0 g (0.02 mole) 1,1,2,2-tetrachloroethylsulfenyl chloride and 0.5 g benzyltriethylammonium chloride in 150 ml methylene chloride, cooled by an ice bath, 10 ml water was added; then 1.6 g (0.02 moles) 50% sodium hydroxide was added dropwise. The reaction mixture was stirred and allowed to come to room temperature overnight. The reaction mixture was washed twice with equal amounts (about 150 ml) water, dried over magnesium sulfate, filtered and stripped. The solid residue was washed with petroleum ether and then dried to give 3.3 g of the above-identified product as a beige solid.

Workup

  1. temperaturecooled by an ice bath
  2. washThe reaction mixture was washed twice with equal amounts (about 150 ml) water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. washThe solid residue was washed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-3f1fac2191294314bb8b11752f978572
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

Loading…