Triethylamine → 3-[4-(4-Hydroxy-3-carboxybenzenesulfonamido)-benzenesulfonyl]acrylonitrile

HRID 267587Notes

Reaction equation

HRID 267587 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13]#[N:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][C:17]=1[C:26]([OH:28])=[O:27].C(N(CC)CC)C>CC(C)=O>[OH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([S:8]([CH:11]=[CH:12][C:13]#[N:14])(=[O:10])=[O:9])=[CH:6][CH:7]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27772405-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 544715203-[4-(4-Hydroxy-3-carboxybenzenesulfonamido)-benzenesulfonyl]acrylonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

is prepared by dissolving 10.4 grams (0.05 mol) of 3-(4-aminobenzenesulfonyl)acrylonitrile and 14 g (0.05 mol + 15% excess) of 4-hydroxy-3-carboxybenzenesulfonyl chloride in 200 ml acetone, cooling in an ice bath and slowly adding thereto 8 ml (0.055 mol) of triethylamine diluted with 25 ml acetone. After filtration and evaporation of the acetone the remaining semi-solid is dissolved in dimethylformamide, dispersed in water and the emulsion extracted with chloroform. After work-up the above sulfonamide is recovered.

Workup

  1. customis prepared
  2. temperaturecooling in an ice bath
  3. additionslowly adding
  4. filtrationAfter filtration and evaporation of the acetone the remaining semi-solid
  5. dissolutionis dissolved in dimethylformamide
  6. additiondispersed in water
  7. extractionthe emulsion extracted with chloroform
  8. customAfter work-up the above sulfonamide is recovered

Sources & evidence

ORD record
ord-d4ae444c4c47440793f3ba6116ed90f3
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

Loading…