Hydrochloric Acid → 3-[(3-Carboxypropyl)amino]-4-phenoxy-5-sulfamoylbenzoic acid

HRID 1111781Notes

Reaction equation

HRID 1111781 reaction equation
ClCCCC([NH:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([S:24](=[O:27])(=[O:26])[NH2:25])[C:16]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]([OH:13])=[O:12])=O.Cl[CH:29]([CH2:33][CH3:34])[C:30](N)=[O:31].[OH-:35].[K+].Cl>O>[O:17]([C:16]1[C:15]([S:24](=[O:26])(=[O:27])[NH2:25])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[NH:7][CH2:34][CH2:33][CH2:29][C:30]([OH:35])=[O:31])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 70589091HCID 70589091, compound

Product 1

HCID 203345343-[(3-Carboxypropyl)amino]-4-phenoxy-5-sulfamoylbenzoic acidYield 120.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The chlorobutyramide 3-(γ-chlorobutyrylamino)-4-phenoxy-5-sulfamylbenzoic acid (11.0 g) was added to a solution of KOH (40 g) in water 100 ml. The resulting solution was stirred and heated under reflux overnight. After cooling it was acidified with 3N acqueous HCl, chilled by adding ice and the product collected, washed and air-dried. A recrystallization from aq. acetone gave 9.80 g (77% on two steps) of N-(2-phenoxy-3-sulfamyl-5-carboxyphenyl)-γ-aminobutyric acid as colorless crystals with m.p. 240°-241°; ir (Nujol) 3400, 3300, 2600 (broad), 1700, 1610, 1590, and 1550 cm-1 ; nmr (CDCl3 /d6 -DMSO) 1.4-2.3 (m, 4H), 3.15 (m, 2H), 4.2 (broad, NH), 6.43 (s, SO2NH2), 6.65-7.4 (m, C6H5), 7.57 (d, J=2, CH), and 7.92 ppm (d, CH); mass spectrum m/e 283 (100%) and 394 (M+ ).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling it
  4. temperaturechilled
  5. additionby adding ice
  6. customthe product collected
  7. washwashed
  8. customair-dried
  9. customA recrystallization from aq. acetone

Sources & evidence

ORD record
ord-71fec2b026e9412a89f7d36f3fdba96b
Source dataset
uspto-grants-1978_10
Patent number
US04118587

Reaction notes

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