Methanesulfonyl chloride → 3-(4-Methanesulfonamidobenzenesulfonyl)acrylonitrile

HRID 267576Notes

Reaction equation

HRID 267576 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH:16]=[CH:17][C:18]#[N:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([CH:16]=[CH:17][C:18]#[N:19])(=[O:15])=[O:14])=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 545373813-(4-Methanesulfonamidobenzenesulfonyl)acrylonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolvent

Procedure

23 grams (0.2 mol) of methanesulfonyl chloride (CH3SO2Cl) are dissolved in 600 milliliters of chloroform, and 42 grams (0.2 mol) of 3-(4-aminobenzenesufonyl)acrylonitrile, prepared as described in copending application Ser. No. 228,410 filed Feb. 22, 1972, are added with stirring and cooling in an ice bath followed portionwise by a solution of 16 g (0.2 mol) of pyridine in 200 ml of pyridine. The reaction mixture is allowed to reach room temperature and is thereafter left at about 20° C for about 48 hours. The solution is filtered and then washed with water, a 5% solution of HCl in water, a 5% sodium bicarbonate solution in water, and water, in sequence.

Workup

  1. addition22, 1972, are added
  2. temperaturecooling in an ice bath
  3. customto reach room temperature
  4. filtrationThe solution is filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-54d081fb94394428a82071b0204d67a2
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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