Water → HCID 53973457, compound

HRID 1604864Notes

Reaction equation

HRID 1604864 reaction equation
[C:1]([NH:10][NH2:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].N1C=CC=CC=1.[CH2:18]([O:20][C:21](Cl)=[O:22])[CH3:19].O>CC(N(C)C)=O>[CH2:18]([O:20][C:21]([N:10]([C:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[NH2:11])=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 13637Salicylic acid, hydrazide

Product 1

HCID 53973457HCID 53973457, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

30.4 g. of salicylic acid hydrazide are dissolved in 200 ml of dimethylacetamide and 16 g of pyridine and 22 g of chloroformic acid ethyl ester are then added simultaneously over the course of 30 minutes. Thereafter the reaction mixture is heated to 80°-90° C for 5 hours whilst stirring and is then cooled to room temperature, and about 500 ml of water are added carefully. Hereupon the N-salicyloyl-hydrazine-carboxylic acid ethyl ester produced (Stabiliser No. 1) separates out as a micro-crystalline precipitate. The compound is isolated and is purified by washing with water and recrystallised from ethanol. Melting point 126° C.

Workup

  1. temperatureThereafter the reaction mixture is heated to 80°-90° C for 5 hours

Sources & evidence

ORD record
ord-494e169dfde847c98d3a237005b38370
Source dataset
uspto-grants-1976_04
Patent number
US03948854

Reaction notes

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