Hydrochloric Acid → HCID 20500796, compound

HRID 851660Notes

Reaction equation

HRID 851660 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](F)=[O:26].Cl>CCOCC>[F:20][C:21]([F:31])([F:32])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676063-(Trifluoromethyl)benzoyl fluorideHCID 130258158-(4-Methoxyphenylamino)-caprylic acid

Product 1

HCID 20500796HCID 20500796, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

6.1 g (23 mmol) of 8-(4-Methoxyphenylamino)-caprylic acid are dissolved in 40 cc. of 0.2 n soda lye. A solution of 4.4 g (23 mmol) of 3-(Trifluoromethyl)-benzoic acid fluoride in 50 cc. of ether are added thereto within 20 minutes with vivid stirring dropwise at 25° C., holding the pH at between 7.2 and 8 by the dropwise addition of 0.2 n soda lye. After the addition, vivid stirring is continued for 30 minutes. The mixture is then acidified to pH 3 by the addition of 2 n hydrochloric acid. The aqueous and ethereal layers are separated. The aqueous phase is extracted several times with ether and then is rendered alkaline by the addition of calcium hydroxide. The separated calcium fluoride is filtered off with suction and is discarded. The purified ethereal phase is shaken with water, dried over MgSO4 and the solvent is distilled off. The residue is purified chromatographically on silicic acid gel using chloroform as eluant.

Workup

  1. additionby the dropwise addition of 0.2 n soda lye
  2. additionAfter the addition
  3. stirringvivid stirring
  4. waitis continued for 30 minutes
  5. customThe aqueous and ethereal layers are separated
  6. extractionThe aqueous phase is extracted several times with ether
  7. additionby the addition of calcium hydroxide
  8. filtrationThe separated calcium fluoride is filtered off with suction
  9. stirringThe purified ethereal phase is shaken with water
  10. dry with materialdried over MgSO4
  11. distillationthe solvent is distilled off
  12. customThe residue is purified chromatographically on silicic acid gel

Sources & evidence

ORD record
ord-ee0feb31a7cd4d58a8e68e143d13769a
Source dataset
uspto-grants-1983_05
Patent number
US04386031

Reaction notes

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