Amfenac → Sodium (2-amino-3-benzoylphenyl)acetate--water (1/1/1)

HRID 2051886Notes

Reaction equation

HRID 2051886 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].[OH-].[Na+:21].[Na]>O1CCCC1>[OH2:15].[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O-:19])=[O:18].[Na+:21]

Participants

5

Reactant 3

HCID 2136AmfenacHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 23663941Sodium (2-amino-3-benzoylphenyl)acetate--water (1/1/1)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 111 g. of 2-amino-3-benzoylphenylacetic acid in 777 ml. of tetrahydrofuran was treated with 31.3 g. of 50% sodium hydroxide solution. The sodium salt began to separate after fifteen minutes. After three hours stirring using an ice bath, the sodium salt was collected and dried (64.0 g., m.p. 245°-252° C.). The salt was recrystallized by adding 1 gm. of salt to 10 ml. of refluxing 95% ethanol followed by the addition of 5 ml. of hot isopropyl ether. After several hours cooling the salt is collected and air dried. The recrystallized salt (90% recovery) melted at 254°-255.5° C.

Workup

  1. customto separate after fifteen minutes
  2. customthe sodium salt was collected
  3. customdried (64.0 g., m.p. 245°-252° C.)
  4. customThe salt was recrystallized
  5. additionby adding 1 gm
  6. temperatureof refluxing 95% ethanol
  7. additionfollowed by the addition of 5 ml
  8. temperatureAfter several hours cooling the salt
  9. customis collected
  10. customair dried

Sources & evidence

ORD record
ord-7a03f1dae9134487860c330284e9d652
Source dataset
uspto-grants-1980_01
Patent number
US04182774

Reaction notes

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