Dichloromethane → HCID 67024354, compound

HRID 389095Notes

Reaction equation

HRID 389095 reaction equation
C1C=CC2N(O)[N:8]=[N:7]C=2C=1.[F:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][C:24]=1[F:25])[O:15][C:16]([CH3:21])([CH3:20])[C:17](O)=[O:18].C(OC(C)(C)C)(=O)NN.[Cl:35]CCl>>[ClH:35].[F:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][C:24]=1[F:25])[O:15][C:16]([CH3:21])([CH3:20])[C:17]([NH:7][NH2:8])=[O:18]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 22270741605680-38-4

Product 1

HCID 67024354HCID 67024354, compound

Procedure

WSC•monohydrochloride (7.84 g) and HOBt (4.25 g) were added to a solution of 2-(3,4-difluorophenoxy)-2-methylpropanoic acid (6.80 g) in dichloromethane (60 ml), followed by stirring at room temperature for one hour, tert-butyl carbazate (4.57 g) was added thereto, followed by stirring at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure and ethyl acetate was then added thereto, the organic layer was washed with water, 0.5M hydrochloric acid, saturated aqueous sodium bicarbonate solution-water (1:1) and then saturated brine in this order, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting oil (10.2 g) was dissolved in ethyl acetate, 4M hydrogen chloride-ethyl acetate was added thereto, followed by stirring at room temperature for 5 hours, and then concentrated under reduced pressure. Ethyl acetate was added thereto, followed by stirring and collecting by filtration, to obtain, as a colorless solid, 2-(3,4-difluorophenoxy)-2-methylpropanohydrazide monohydrochloride (8.11 g).

Workup

  1. stirringby stirring at room temperature for 14 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure and ethyl acetate
  3. additionwas then added
  4. washthe organic layer was washed with water, 0.5M hydrochloric acid, saturated aqueous sodium bicarbonate solution-water (1:1)
  5. dry with materialsaturated brine in this order, and then dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe resulting oil (10.2 g) was dissolved in ethyl acetate
  8. addition4M hydrogen chloride-ethyl acetate was added
  9. stirringby stirring at room temperature for 5 hours
  10. concentrationconcentrated under reduced pressure
  11. additionEthyl acetate was added
  12. stirringby stirring
  13. filtrationcollecting by filtration

Sources & evidence

ORD record
ord-7d7745ce29954d0b9c83c3b2fddb9657
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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