Water → HCID 68535315, compound

HRID 1993684Notes

Reaction equation

HRID 1993684 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[N:8]2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27]>C(OCC)(=O)C>[Cl:31][C:30]([Cl:33])([Cl:32])[CH2:29][O:28][C:26](=[O:27])[NH:12][C:11]1[N:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=2)[N:8]=[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 68540206HCID 68540206, compound

Product 1

HCID 68535315HCID 68535315, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Place 2-p-tolyl-5-trimethylsilanyl-2H-pyrazol-3-ylamine (170 mg, 0.693 mmol) in ethyl acetate (10 mL). Add potassium carbonate (191 mg, 1.38 mmol) and water (2 mL). Stir the reaction and add trichloroethyl chloroformate (0.114 mL, 0.831 mmol). Stir at room temperature for 18 hours. Add water and ethyl acetate. Separate organic layer and wash with saturated aq. sodium chloride. Collect organic layer, dry over Mg2SO4, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with 0-30% EtOAc:hexane to yield 280 mg (96%) of the title compound. MS(ES+): m/z=420.2 [M+H].

Workup

  1. customthe reaction
  2. stirringStir at room temperature for 18 hours
  3. washSeparate organic layer and wash with saturated aq. sodium chloride
  4. dry with materialCollect organic layer, dry over Mg2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography eluting with 0-30% EtOAc

Sources & evidence

ORD record
ord-37e275c0e8a94250bb4b2f15aae55ccc
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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