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

HRID 1833716Notes

Reaction equation

HRID 1833716 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-02baf3ecd7674999909516370f1fd164
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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