Hydrazine hydrate (1:1) → alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetohydrazide

HRID 1198910Notes

Reaction equation

HRID 1198910 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6](OCC)=[O:7].O.[NH2:24][NH2:25]>C(O)C>[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([NH:24][NH2:25])=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14370696Ethyl alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate

Product 1

HCID 14370703alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetohydrazideYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.0 g of ethyl α-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate (prepared as described in Example 5) and 0.39 g of 80% hydrazine hydrate in 10 ml of ethanol was stirred on an oil bath kept at 105° C. for 4 hours. The mixture was then cooled, after which the crystals which precipitated were collected by filtration and recrystallized from ethanol, to give 0.73 g of the title compound as white crystals melting at 252°-254° C.

Workup

  1. temperatureThe mixture was then cooled
  2. customafter which the crystals which precipitated
  3. filtrationwere collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f9a4718fc6454e47b7b43ea5fc2fd283
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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