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

HRID 1706800Notes

Reaction equation

HRID 1706800 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 3 N 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-8b695c1ce0794fe283c6154f7a7c32b6
Source dataset
uspto-grants-1980_06
Patent number
US04208535

Reaction notes

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