Sodium Hydroxide → HCID 69111299, compound

HRID 2200059Notes

Reaction equation

HRID 2200059 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH2:11][CH3:12])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17]>C(OCC)(=O)C.O>[Cl:21][C:20]([Cl:23])([Cl:22])[CH2:19][O:18][C:16](=[O:17])[NH:10][C:8]1[N:7]([CH2:11][CH3:12])[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 612657223-(1,1-Dimethylethyl)-1-ethyl-1H-pyrazol-5-amine

Product 1

HCID 69111299HCID 69111299, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 3-tert-butyl-1-ethyl-1H-pyrazole-5-amine (0.500 g, 2.99 mmol) in ethyl acetate (7.5 mL) and 1 M aqueous NaOH (7.5 mL, 7.5 mmol), cooled in an ice bath, was added 2,2,2-trichloroethyl chloroformate (0.453 mL, 3.29 mmol) and the mixture was stirred for 45 min. The mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were dried (MgSO4) and evaporated. The residue was crystallised from pentane-diethyl ether (1:1) to give the title compound (0.078 g) as a white solid. The mother liquors were evaporated and purified by column chromatography (0-40% EtOAc/cyclohexane) to give the title compound (0.817 g) as a colorless oil (Total yield 0.895 g, 87%). LCMS (Method 3): Rt 4.09 min, m/z 342/344/346 [MH+]. 1H NMR (300 MHz, CDCl3): 1.44 (12H, m), 4.78-4.83 (2H, m), 4.88 (2H, s), 6.53 (1H, s), 9.82 (1H, s).

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated
  5. customThe residue was crystallised from pentane-diethyl ether (1:1)

Sources & evidence

ORD record
ord-739d4aa8778e4236b89261b78cdf18e2
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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