Water → Ethyl [[2-[3,5-dichloro-4-[1-[5-(2-methylphenyl)-1,2,4-oxadiazol-3-yl]-1-methylethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazin-6-yl]carbonyl]carbamate

HRID 1072482Notes

Reaction equation

HRID 1072482 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:24][N:25]=[C:26]([C:35]([NH:37][C:38](=[O:42])OCC)=[O:36])[C:27]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])=[O:28])[CH:5]=[C:6]([Cl:23])[C:7]=1[C:8]([C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[O:13][N:12]=1)([CH3:10])[CH3:9].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Cl:23][C:6]1[CH:5]=[C:4]([N:24]2[C:38](=[O:42])[NH:37][C:35](=[O:36])[C:26]([C:27]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])=[O:28])=[N:25]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]([C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[O:13][N:12]=1)([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 22386569diethyl N,N'-[2-[[3,5-dichloro-4-[1-[5-(2-methylphenyl)-1,2,4-oxadiazol-3-yl]-1-methylethyl]phenyl]hydrazono]-1,3-dioxo-1,3-propanediyl]dicarbamate

Product 1

HCID 86588468Ethyl [[2-[3,5-dichloro-4-[1-[5-(2-methylphenyl)-1,2,4-oxadiazol-3-yl]-1-methylethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazin-6-yl]carbonyl]carbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of intermediate (20) (0.0302 mole) and sodium acetate (0.0302 mole) in acetic acid (200 ml) was stirred and refluxed for 3 hours. The reaction mixture was poured out into water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. Toluene was added and azeotroped on the rotary evaporator, yielding ethyl [[2-[3,5-dichloro-4-[1-[5-(2-methylphenyl)-1,2,4-oxadiazol-3-yl]-1-methylethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazin-6-yl]carbonyl]carbamate (intermediate 21).

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionthis mixture was extracted with CH2Cl2
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. additionToluene was added
  7. customazeotroped on the rotary evaporator

Sources & evidence

ORD record
ord-2f3814f355334a70b36dd3af29fc90ab
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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