Sodium Iodide → 11-[4-Chloro-N-(4-methoxyphenyl)-benzamido]-undecanoic acid methyl ester

HRID 851656Notes

Reaction equation

HRID 851656 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+].[CH3:21][O:22][C:23](=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br.[I-].[Na+]>CN(C)C=O>[CH3:21][O:22][C:23](=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][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 5238Sodium IodideHCID 24758Sodium hydrideHCID 2218484-Chloro-N-(4-methoxyphenyl)benzamideHCID 223913Methyl 11-bromoundecanoate

Product 1

HCID 5376877711-[4-Chloro-N-(4-methoxyphenyl)-benzamido]-undecanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As described in example 1(a), the reaction is carried out with 28.7 g (0.11 mol) of 4-chloro-N-(4-methoxyphenyl)-benzamide, 4.5 g (0.18 mol) of sodium hydride, 36.7 g (0.13 mol) of 11-bromoundecanoic acid methyl ester, 100 cc. of dimethylformamide and 3 g (0.02 mol) of sodium iodide. Reaction time: 5 hours, reaction temperature: 80° C. The crude product is used in the next step without further purification.

Workup

  1. customReaction time
  2. custom5 hours, reaction temperature
  3. custom80° C
  4. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-2bbc21696e9d4ecea78e99c5f72b5e1d
Source dataset
uspto-grants-1983_05
Patent number
US04386031

Reaction notes

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