Sulfuric Acid → HCID 53784359, compound

HRID 267580Notes

Reaction equation

HRID 267580 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.NC1C=CC(S(C(=C)C#N)(=O)=O)=CC=1.S(=O)(=O)(O)O.C(N(CC)CC)C.[C:42]1([CH3:52])[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=1>CN(C)C=O.O>[CH3:52][C:42]1[CH:47]=[CH:46][C:45]([S:48]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)(=[O:50])=[O:49])=[CH:44][CH:43]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21516747HCID 21516747, compoundHCID 54231039HCID 54231039, compound

Product 1

HCID 53784359HCID 53784359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

22.6 g (0.1 mol) of 3-(4-aminobenzenesulfonyl)acrylamide, prepared by hydrolysis of 3-(4-aminobenzenesulfonyl acrylonitrile with a 1:1 molar mixture of concentrated sulfuric acid and water, is dissolved in dimethylformamide (100 ml), and 14.5 ml triethylamine (0.1 mol) are added thereto. A solution of p-toluenesulfonyl chloride (19.1 g, 0.1 mol) in 50 ml dimethylformamide is added dropwise at room temperature, and the reaction mixture is left undisturbed for 16 hours. The product is recovered by precipitation with water and recrystallization from ethanol. There is thus produced 3-[4-(4-methylbenzenesulfonamido)benzenesulfonyl]acrylamide: ##SPC14##

Workup

  1. customThe product is recovered by precipitation with water and recrystallization from ethanol

Sources & evidence

ORD record
ord-32e9f0b13e5d494e89a6244be97cda52
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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