Triethylamine → N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-isophthalic acid monoamide

HRID 2380682Notes

Reaction equation

HRID 2380682 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)#[N:2].[Cl-].CO[C:23](=[O:33])[C:24]1[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([OH:29])=[O:28])[CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][CH2:18][CH3:19])[C:23](=[O:33])[C:24]2[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([OH:29])=[O:28])[CH:25]=2)=[CH:13][CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amineHCID 86748168Isophthalic acid monomethyl ester chloride

Product 1

HCID 54327068N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-isophthalic acid monoamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.50 g of N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine, 2.98 g of isophthalic acid monomethyl ester monochloride and 2.10 ml of triethylamine in 100 ml of CH2Cl2 is stirred at room temperature for 1 hour. Extraction twice with 50 ml of water each time and customary treatment of the organic phase yields a crude product that, after chromatography on silica gel 60 (40-63 μm) using CH2Cl2 as eluant, yields N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-isophthalic acid monoamide that has an Rf value of 0.61 [CH2Cl2 /CH3OH (4:1)].

Workup

  1. extractionExtraction twice with 50 ml of water each time and customary treatment of the organic phase
  2. customyields a crude product that

Sources & evidence

ORD record
ord-bb00ac8147284815bbe76c8411d83de1
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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