Diiodomethane → HCID 178469927, compound

HRID 1842571Notes

Reaction equation

HRID 1842571 reaction equation
N[C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[I:12]CI.N(OCCC(C)C)=O>C(OCC)(=O)C>[I:12][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 178469928HCID 178469928, compound

Product 1

HCID 178469927HCID 178469927, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-amino-1H-pyrazole-4-carboxylate (10.0 g, 64.5 mmol) in diiodomethane (130 mL, 1.61 mol) at −10° C. was added isoamyl nitrite (156.0 mL, 1.16 mol). The mixture was allowed to warm to ambient temperature then heated to 100° C. After 2 h, ethyl acetate was added. The mixture was washed with saturated aqueous Na2SO3, HCl (1N in water) then water. The organic layer was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (9.63 g). MS 267.1 (M+1).

Workup

  1. temperaturethen heated to 100° C
  2. washThe mixture was washed with saturated aqueous Na2SO3, HCl (1N in water)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9fd00594ce90454f8a311f311f765a91
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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