Acetic Acid → 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-triazine-6-carboxylic acid

HRID 1072483Notes

Reaction equation

HRID 1072483 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[C:29](=[O:30])[NH:28][C:27](=[O:31])[C:26]([C:32](NC(=O)OCC)=[O:33])=[N:25]2)[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:42])C>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[C:29](=[O:30])[NH:28][C:27](=[O:31])[C:26]([C:32]([OH:33])=[O:42])=[N:25]2)[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)([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 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

Product 1

HCID 98706642-[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-triazine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of intermediate (21) (0.0302 mole) in HCl 36% (10 ml) and acetic acid (200 ml) was stirred and refluxed overnight. The reaction mixture was poured out onto crushed ice and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated, yielding 16.3 g of 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-triazine-6-carboxylic acid (intermediate 22).

Workup

  1. temperaturerefluxed overnight
  2. additionThe reaction mixture was poured out
  3. customonto crushed ice
  4. extractionthis mixture was extracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-461cfc84cf5b49a5a1f4610cd69fa8df
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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