Formic Acid → N-[1-[3-(Formyloxy)propyl]-1H-pyrazol-5-yl]formamide

HRID 2082025Notes

Reaction equation

HRID 2082025 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][OH:10])[N:5]=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])C.[CH:18](O)=[O:19].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH:11]([NH:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][O:10][CH:18]=[O:19])[N:5]=[CH:4][CH:3]=1)=[O:13]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 14996572HCID 14996572, compound

Product 1

HCID 14996573N-[1-[3-(Formyloxy)propyl]-1H-pyrazol-5-yl]formamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Amino-1-(3-hydroxypropyl)pyrazole (5.3 g) was added to a mixture of acetic anhydride (8.86 ml) and formic acid (7.08 ml) under ice-cooling. The mixture was stirred for two hours at room temperature. The reaction mixture was added to a mixture of ice-water (30 ml), ethyl acetate (30 ml) and tetrahydrofuran (60 ml), and an aqueous solution of potassium carbonate was added thereto to adjust the pH of the mixture to 7. The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 5-formamido-1-(3-formyloxypropyl)pyrazole (6.74 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-863e0b7b6bd24580b813e6323876fd3b
Source dataset
uspto-grants-1993_02
Patent number
US05187160

Reaction notes

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