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

HRID 1704340Notes

Reaction equation

HRID 1704340 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 15 minutes. After 3 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 15 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-6dceee355d564f1c99d8d0c6a6964413
Source dataset
uspto-grants-1978_11
Patent number
US04126635

Reaction notes

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