Water → N-(2,5-dihydroxybenzoyl)-hydrazinecarboxylic acid octadecyl ester

HRID 1604865Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[CH2:13]([O:31][C:32](Cl)=[O:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C.O>CC(N(C)C)=O>[CH2:13]([O:31][C:32]([N:6]([C:4](=[O:5])[C:3]1[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:2]=1[OH:1])[NH2:7])=[O:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 40 °C

Procedure

33.6 g of 2,5-dihydroxybenzoic acid hydrazide are dissolved in 150 ml of dimethylacetamide and 66.5 g of chloroformic acid octadecyl ester in 150 ml of dimethylacetamide, and 21 g of triethylamine, are added simultaneously over the course of 30 minutes. Thereafter the reaction mixture is warmed to 40° C for 3 hours whilst stirring, cooled and poured into 2 litres of water. The N-(2,5-dihydroxybenzoyl)-hydrazinecarboxylic acid octadecyl ester obtained (Stabiliser No. 8) forms a pulverulent precipitate which is isolated, washed with water, dried at 80° C and recrystallised from isopropanol. Melting point 163° C.

Workup

temperaturecooled

Sources & evidence

ORD record: ord-c03b6027bbb6462c80e3394a1d6bc421
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03948854

Reaction notes

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