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

HRID 1198902Notes

Reaction equation

HRID 1198902 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:34])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=O)[CH:24]([NH:26][C:27]([O:29]CC)=O)[CH3:25])=[CH:19][C:18]=2[Cl:33])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.[NH2:36][NH2:37]>C(O)CCC>[Cl:33][C:18]1[CH:19]=[C:20]([C:23]2[CH:24]([CH3:25])[NH:26][C:27](=[O:29])[NH:36][N:37]=2)[CH:21]=[CH:22][C:17]=1[O:16][CH2:15][C:14]([NH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:34]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14370692N-[2-(3,4-Dimethoxyphenyl)ethyl]-alpha-{2-chloro-4-[2-(ethoxycarbonylamino)propionyl]phenoxy}acetamide

Product 1

HCID 14370693alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamideYield 21.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 556 mg of N-[2-(3,4-dimethoxyphenyl)-ethyl]-α-{2-chloro-4-[2-(ethoxycarbonylamino)propionyl]phenoxy}acetamide [prepared as described in step (c) above] and 723 mg of hydrazine hydrate in 7 ml of butanol was heated under reflux for 67 hours. At the end of this time, the mixture was cooled, and the butanol used as the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 10:1 by volume mixture of chloroform and methanol, to give 112 mg of the title compound as a white powder melting at 167°-169° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 67 hours
  3. temperatureAt the end of this time, the mixture was cooled
  4. customwas removed by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel
  6. washeluted with a 10:1 by volume mixture of chloroform and methanol

Sources & evidence

ORD record
ord-1f53aa30cbd04b579494b97b450a5dea
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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