Nitric Acid → HCID 54164578, compound

HRID 267577Notes

Reaction equation

HRID 267577 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]=[CH:15][C:16]#[N:17])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.S(=O)(=O)(O)O.[N+:23]([O-])([OH:25])=[O:24]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]=[CH:15][C:16]#[N:17])(=[O:13])=[O:12])=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 54557110HCID 54557110, compound

Product 1

HCID 54164578HCID 54164578, compound

Procedure

3-(4-acetamidobenzenesulfonyl)acrylonitrile, prepared as described in the aforesaid U.S. Pat. No. 3,541,119, is nitrated at about room temperature in a mixture of nitric acid and concentrated sulfuric acid for about two hours, and thereafter drowned in ice water. The 2-cyanovinyl 4-acetamido-3-nitrophenyl sulfone recovered is hydrolyzed in a mixture of dilute hydrochloric acid and ethanol to give 2-cyanovinyl 4-amino-3-nitrophenyl sulfone. 25.3 g (0.1 mol) of this material is carefully dried and is dispersed in 500 ml chloroform and 11.2 g 1,4-diaza-[2.2.2]octane is added thereto. A chloroform solution of difluoromethanesulfonyl chloride in about 10% excess is added to the stirred mixture of the substituted aminoarene and the acid acceptor at 50° C. The mixture is stirred at this temperature for 2 hours and is then maintained at room temperature for 2 days. After treatment with dilute HCl to remove the tertiary amine and unreacted starting material, and evaporation of the solvent, a crude material is obtained which is purified by recrystallization, giving 2-cyanovinyl 4-difluoroacetamido-3-nitrophenyl sulfone: ##SPC7##

Workup

  1. customThe 2-cyanovinyl 4-acetamido-3-nitrophenyl sulfone recovered
  2. additionis hydrolyzed in a mixture of dilute hydrochloric acid and ethanol

Sources & evidence

ORD record
ord-9d52a3f5833d47c79ce312180f704691
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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