Sodium ethoxide → 4-(4-n-Heptylpyrimid-2-yl)-benzoic acid

HRID 1973583Notes

Reaction equation

HRID 1973583 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[NH:14])[NH2:13])=[CH:8][CH:7]=1)[CH3:3].[CH2:16]([C:23](=[CH:26]OCC)C=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH3:30]C[O-].[Na+]>CO>[CH2:2]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:23]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:26]=[CH:30][N:14]=2)=[CH:8][CH:7]=1)[CH3:3].[CH2:17]([C:16]1[CH:23]=[CH:26][N:13]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]([C:5]([OH:4])=[O:15])=[CH:11][CH:10]=2)[N:14]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:30]

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 12710118Benzoic acid, 4-(aminoiminomethyl)-, ethyl ester, hydrochloride (1:1)HCID 542398243-Ethoxy-2-heptylacrolein

Product 2

HCID 203796744-(4-n-Heptylpyrimid-2-yl)-benzoic acidHCID 543719414(4-n-Heptylpyrimid-2-yl)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 0.1 mole of 4-amidino-benzoic acid ethyl ester hydrochloride, 0.1 mole of 2-n-heptyl-3-ethoxy-acrolein and 0.14 mole of sodium ethylate in 100 ml of methanol is stirred overnight at room temperature under an atmosphere of nitrogen. After the usual work up and separation into basic and acidic fractions, there is obtained 4-(4-n-heptylpyrimid-2-yl)-benzoic acid ethyl ester and 4-(4-n-heptylpyrimid-2-yl)-benzoic acid.

Workup

  1. customAfter the usual work up and separation into basic and acidic fractions

Sources & evidence

ORD record
ord-28d29e795aa742a5aab166cc4ae5a2bc
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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