Diflunisal → 1-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

HRID 1719726Notes

Reaction equation

HRID 1719726 reaction equation
C(N(CC)CC)C.[CH:8]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]([F:21])=[CH:18][C:19]=2[F:20])=[CH:12][C:11]([C:22]([OH:24])=[O:23])=[C:10]([OH:25])[CH:9]=1.[C:26](=[O:34])([O:31][CH2:32][CH3:33])[O:27][CH:28](Cl)[CH3:29]>CO>[F:20][C:19]1[CH:18]=[C:17]([F:21])[CH:16]=[CH:15][C:14]=1[C:13]1[CH:12]=[C:11]([C:22]([O:24][CH:28]([O:27][C:26]([O:31][CH2:32][CH3:33])=[O:34])[CH3:29])=[O:23])[C:10]([OH:25])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3059DiflunisalHCID 8471TriethylamineHCID 162095Carbonic acid, 1-chloroethyl ethyl ester

Product 1

HCID 134913951-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.76 g of the triethylamine salt of diflunisal and 1.0 g of 1-chloroethyl ethyl carbonate are heated in an oil bath at 100°-110° with magnetic stirring for 3 hours. The reaction mixture is then cooled to room temperature and 5 ml of methanol are added. After cooling to 0°-5°, the resulting precipitate is collected by filtration, washed with 3 ml of cold methanol then with 5 ml of 10% ethyl ether in hexane. After air drying there is obtained 1.38 g (75%) of 1-(ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate, m.p. 76°-78°.

Workup

  1. temperatureare heated in an oil bath at 100°-110°
  2. temperatureAfter cooling to 0°-5°
  3. filtrationthe resulting precipitate is collected by filtration
  4. washwashed with 3 ml of cold methanol
  5. customAfter air drying there

Sources & evidence

ORD record
ord-07459748691c47a39b82ec764164ad0d
Source dataset
uspto-grants-1985_09
Patent number
US04542158

Reaction notes

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