Acetone → HCID 20334538, compound

HRID 1111783Notes

Reaction equation

HRID 1111783 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].[CH:22]([C:24]([CH3:26])=[O:25])=[CH2:23].CC(C)=O>C(O)C>[O:25]=[C:24]([CH3:26])[CH2:22][CH2:23][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

5

Reactant 3

HCID 180AcetoneHCID 6570Methyl vinyl ketoneHCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Product 1

HCID 20334538HCID 20334538, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-4-phenoxy-5-sulfamylbenzoic acid (5 g) and methyl vinyl ketone (5 ml) in ethanol (100 ml) was stirred at reflux for 3 days. After cooling, the product 3-(γ-oxobutylamino)-4-phenoxy-5-sulfamylbenzoic acid was collected to give 5.05 g (82%) in two crops of colorless solid. An analytical sample from aq. acetone had m.p. 215°-215.5°; ir (Nujol) 3400, 3250, 1710, 1695, 1615, 1590, and 1570 cm-1 ; nmr (CDCl3 /d6 -DMSO/D2O-washed) 2.00 (s, CH3), 2.60 (t, CH2), 3.37 (t, CH2), 6.8-7.4 (m, C6H5), 7.60 (d, J=2, CH), and 7.93 (d, CH); mass spectrum was of decomposition products, 308 (100%).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureAfter cooling
  3. customthe product 3-(γ-oxobutylamino)-4-phenoxy-5-sulfamylbenzoic acid was collected
  4. customto give 5.05 g (82%) in two crops of colorless solid

Sources & evidence

ORD record
ord-51d5c8de5e894eafb00e433a69bf4884
Source dataset
uspto-grants-1978_10
Patent number
US04118587

Reaction notes

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