Hydrochloric Acid → HCID 178442854, compound

HRID 2372894Notes

Reaction equation

[CH2:1](OCCO)C.C/[C:8](/N)=[CH:9]\[C:10]#[N:11].[C:13]([CH2:15][C:16]([NH:18][NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=O)#[N:14].Cl.[OH2:40]>[Cl-].[Zn+2].[Cl-]>[C:13]([C:15]1[C:8]([OH:40])=[CH:9][C:10]2[N:18]([N:19]=[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[N:11]=2)[C:16]=1[CH3:1])#[N:14]

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 1000 ml of ethylene glycol monoethyl ether, 120 g of 3-aminocrotonitrile and 365 g of N-cyanoacetyl-N'-stearoylhydrazine was heated to 135° C. within 2 hours and then refluxed for a further 2 hours. Addition of 150 g of anhydrous zinc chloride and boiling for a further 4 hours were followed by dilution of the melt with 2000 ml of water and addition of 200 ml of 12 % by weight hydrochloric acid. The precipitated product was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. 397 g of 6-cyano-2-heptadecyl-7-hydroxy-5-methyl[1,2,4]triazolo[2,3-a]pyridine were obtained. The compound melts at 274 to 275° C. after recrystallization from acetic acid and has the following analysis:

Workup

temperaturerefluxed for a further 2 hours
filtrationThe precipitated product was filtered off with suction
washwashed with water
customdried at 80° C. under reduced pressure

Sources & evidence

ORD record: ord-1586cfcfde604337a853d00b4d3d440f
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05101028

Reaction notes

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