Dimethylformamide → 8-[4-Chloro-N-(4-methoxyphenyl)-benzamido]-caprylic acid methyl ester

HRID 851652Notes

Reaction equation

HRID 851652 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].CN(C)C=O.[CH3:26][O:27][C:28](=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br>CCOCC>[CH3:26][O:27][C:28](=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:8]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2218484-Chloro-N-(4-methoxyphenyl)benzamideHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 538084338-[4-Chloro-N-(4-methoxyphenyl)-benzamido]-caprylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

As described in example 1(a), the reaction is carried out with 130.7 g (0.5 mol) of 4-chloro-N-(4-methoxyphenyl)-benzamide, 24.5 g (1 mol) sodium hydride, 700 cc. of dimethylformamide and 118.5 g (0.5 mol) of 8-bromocaprylic acid methyl ester. Reaction time and reaction temperature: 5 hours at 80° C., thereafter 12 hours at 100° C. The reaction mixtures are further processed as described in example 1(a). The crude product is dissolved in 300 cc. of ether. After standing for a prolonged period, the unreacted 4-chloro-N-(4-methoxyphenyl)-benzamide separates by crystallisation and is filtered off. The solvent is partly distilled off and the resulting oily crude product (181 g) is separated. 125 g are used in the next step without further purification, the remainder (56 g) is purified chromatographically on silicic acid using chloroform as eluant.

Workup

  1. customReaction time and reaction temperature
  2. custom5 hours
  3. customat 80° C.
  4. custom12 hours
  5. customat 100° C
  6. customThe reaction mixtures
  7. waitAfter standing for a prolonged period
  8. customthe unreacted 4-chloro-N-(4-methoxyphenyl)-benzamide separates by crystallisation
  9. filtrationis filtered off
  10. distillationThe solvent is partly distilled off
  11. customthe resulting oily crude product (181 g) is separated
  12. custom125 g are used in the next step without further purification
  13. customthe remainder (56 g) is purified chromatographically on silicic acid

Sources & evidence

ORD record
ord-0cf40c21efd04d1c9b6d5b71f26b97e9
Source dataset
uspto-grants-1983_05
Patent number
US04386031

Reaction notes

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