3-Amino-4-phenoxy-5-sulfamoylbenzoic acid → HCID 20334532, compound

HRID 1706803Notes

Reaction equation

HRID 1706803 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[Br:22][CH2:23]/[CH:24]=[CH:25]/[CH2:26]Br>O>[Br:22][CH2:23]/[CH:24]=[CH:25]/[CH2:26][NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acidHCID 641245trans-1,4-Dibromo-2-butene

Product 1

HCID 20334532HCID 20334532, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-amino-4-phenoxy-5-sulfamylbenzoic acid (2 g) and 1,4-trans-dibromo-2-butene (3.2 g) in dioxame (35 ml) was heated to reflux overnight. The solvent was removed under reduced pressure and the dark, gummy residue was chromatographed on a silica gel column using chloroform/benzene/acetic acid/methanol (80:10:10:2.5) as the eluting solvent. The fractions containing the product were combined and concentrated leaving an acetic acid solution of it. This was diluted with water to give a cream colored powder which was filtered, dried and washed with pet. ether to remove unreacted dibromobutene. The resulting 3-(4-bromo-trans-2-butenylamino)-4-phenoxy-5-sulfamylbenzoic acid was an off-white solid 0.75 g (26%) with m.p. 191°-194°; ir (Nujol) 3350, 3200, 2600 (broad), 1690, 1605, 1585, and 1530 cm-1 ; nmr (CDCl3 /d6 -DMSO) 3.7-4.5 (m, 5H incl. NH), 5.73 (t, 2H, vinyl), 6.27 (s, SO2NH2), 6.8-7.4 (m, C6H5), 7.57 (d, J=2, CH), and 8.03 ppm (d, CH); mass spectrum is of decomposition products.

Workup

  1. temperatureto reflux overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe dark, gummy residue was chromatographed on a silica gel column
  4. additionThe fractions containing the product
  5. concentrationconcentrated
  6. customleaving an acetic acid solution of it
  7. customto give a cream
  8. filtrationwas filtered
  9. customdried
  10. washwashed with pet. ether
  11. customto remove unreacted dibromobutene

Sources & evidence

ORD record
ord-124913e52b294b2a8a36426127b5a2b7
Source dataset
uspto-grants-1980_06
Patent number
US04208535

Reaction notes

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