Hydrochloric Acid → HCID 53784400, compound

HRID 267581Notes

Reaction equation

HRID 267581 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13](N)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N([CH2:21][CH3:22])CC)C.Cl.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.S(=O)(=O)(O)[OH:36]>CC(C)=O.C(O)C>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13]([O:14][CH2:21][CH3:22])=[O:36])(=[O:10])=[O:9])=[CH:4][CH:3]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 54231039HCID 54231039, compound

Product 1

HCID 53784400HCID 53784400, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 702EthanolSolvent

Procedure

25.5 g (0.1 mol) of ethyl 3-(4-aminobenzenesulfonyl) acrylate, prepared by refluxing 3-(4-aminobenzenesulfonyl)acrylamide in an excess of absolute ethanol and in the presence of concentrated sulfuric acid as a condensing agent, are dissolved in acetone (100 ml). 14.5 ml of triethylamine (0.1 mol) are added as an HCl acceptor. A solution of p-toluenesulfonyl chloride (19.1 g, 0.1 mol) in 50 ml acetone is added dropwise at room temperature. The reaction mixture is left for 12 hours and is then poured into ice water. The precipitated solid is recovered by filtration, dried and recrystallized from ethanol, giving ethyl 3-[4-(4-methylbenzenesulfonamido)benzenesulfonyl]acrylate: ##SPC15##

Workup

  1. filtrationThe precipitated solid is recovered by filtration
  2. customdried
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-97dbb4cf405b4d5989daf047fd52a477
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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