Hydrochloric Acid → HCID 178433724, compound

HRID 1862236Notes

Reaction equation

HRID 1862236 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][CH:5]([C:10](=O)[CH3:11])[C:6](OC)=[O:7].C(OC)(=O)[NH:32][NH2:33].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][C:5]1[C:6]([OH:7])=[N:32][NH:33][C:10]=1[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80519Methyl carbazateHCID 18619261HCID 18619261, compound

Product 1

HCID 178433724HCID 178433724, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.09 g of methyl 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-oxobutyrate and 1.23 g of methyl carbazate were suspended in 30 ml of toluene, and the mixture was heated under reflux for 5 hours. The solution was cooled to room temperature, then, the reaction solution was poured into ice water and dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was washed with a mixed solvent of n-hexane:ethyl acetate (3:1) to obtain 2.94 g of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-hydroxy-5-methylpyrazole.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washThe residue was washed with a mixed solvent of n-hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-08c8e521bd5b41f2bb77a3469eb255f4
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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