p-Anisoyl chloride → 8-[4-Methoxy-N-(4-methoxyphenyl)-benzamido]-caprylic acid methyl ester

HRID 851650Notes

Reaction equation

HRID 851650 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>CCOCC>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 130258148-(4-Methoxyphenylamino)-caprylic acid methyl ester

Product 1

HCID 538841738-[4-Methoxy-N-(4-methoxyphenyl)-benzamido]-caprylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12 g (43 mmol) of 8-(4-methoxyphenylamino)-caprylic acid methyl ester are dissolved in 400 cc. of ether. 5.1 g (50 mmol) of triethylamine are added thereto. 7.3 g (43 mmol) of 4-methoxybenzoic acid chloride are added dropwise to the mixture with stirring and cooling with ice. After the addition, stirring is continued at 25° C. for 5 hours. The separated triethylamine-hydrochloride is filtered off with suction and the ethereal phase is washed in sequence with water, 5% bicarbonate solution, water, 2 n hydrochloric acid and water is dried over Na2SO4, and the solvent is distilled off. The crude product is used in the next step without any further purification.

Workup

  1. temperaturecooling with ice
  2. additionAfter the addition
  3. stirringstirring
  4. filtrationThe separated triethylamine-hydrochloride is filtered off with suction
  5. washthe ethereal phase is washed in sequence with water, 5% bicarbonate solution, water, 2 n hydrochloric acid and water
  6. dry with materialis dried over Na2SO4
  7. distillationthe solvent is distilled off
  8. customThe crude product is used in the next step without any further purification

Sources & evidence

ORD record
ord-faf1e4a5fd024c2ea540906b1e8164f4
Source dataset
uspto-grants-1983_05
Patent number
US04386031

Reaction notes

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