Tetrahydrofuran → HCID 66854111, compound

HRID 251901Notes

Reaction equation

HRID 251901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[CH:13][CH:12]=3)[O:8][C:7](=[O:23])[C:6]=2[CH:24]=1.O.[NH2:27][NH2:28].O1CCCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([NH:10][C:9]([C:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[CH:13][CH:12]=2)=[O:8])=[C:6]([C:7]([NH:27][NH2:28])=[O:23])[CH:24]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 66853841HCID 66853841, compound

Product 1

HCID 66854111HCID 66854111, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.50 g of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one, 0.13 ml of hydrazine monohydrate and 20 ml of tetrahydrofuran was stirred at room temperature for 4 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was washed with a mixed solvent of ethyl acetate and hexane to obtain 0.44 g of N-[4-chloro-2-(hydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting residue was washed with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-7a0ff1ccdb474ff8b1dcb5ff4911d85a
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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