Water → 6-Methyl-3-[1-(4-nitrophenoxy)tridecyl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

HRID 374230Notes

Reaction equation

[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH:9]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:10]([NH:12][NH:13][C:14]2[S:15][CH2:16][C:17]([CH3:20])=[N:18][N:19]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(C)C.O>C(O)(=O)C>[CH3:20][C:17]1[CH2:16][S:15][C:14]2=[N:13][N:12]=[C:10]([CH:9]([O:8][C:7]3[CH:33]=[CH:34][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:19]2[N:18]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 33.0 g of the above substituted acylhydrazine 1b in 132 ml of acetic acid is heated with stirring at 95° C. for 2 hours. At the end of the reaction, 65 ml of isopropyl alcohol is added to the reaction mixture. And then the whole mixture is added with stirring to 200 ml of 70° C. water. After cooling to 20° C. and stirring at that temperature for an hour, the product is collected, washed with water, dried, and recrystallized from isopropyl alcohol to give 27.2 g (47% overall from 3b or 86% from 1b) of 6-methyl3-(1-[4-nitrophenoxy]tridecyl)-7H-1, 2,4 triazolo(3,4-b)-1,3,4 -thiadiazine (4) with 95 area % by HPLC.

Workup

additionis added to the reaction mixture
additionAnd then the whole mixture is added
temperatureAfter cooling to 20° C.
stirringstirring at that temperature for an hour
customthe product is collected
washwashed with water
customdried
customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-b7b2daac92b8479097a044285690b196
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166378

Reaction notes

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