Formic Acid → 5-t-Butyl-3-formylaminopyrazole

HRID 2164495Notes

Reaction equation

HRID 2164495 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][N:3]=1.[CH:11](O)=[O:12]>C1(C)C=CC=CC=1>[C:7]([C:5]1[NH:4][N:3]=[C:2]([NH:1][CH:11]=[O:12])[CH:6]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 5227873-Amino-5-tert-butylpyrazole

Product 1

HCID 132359375-t-Butyl-3-formylaminopyrazoleYield 52.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 14 g (0.1 mole) of 3-amino-5-t-butylpyrazole prepared in Example 1 were added 16.3 g (0.3 mole) of 85% formic acid and 30 ml of toluene, followed by heating under reflux conditions while separating water by distillation. When a calculated amount of water and an excessive amount of formic acid distilled out, the heating was stopped. The reaction mixture was diluted with water and then concentrated as whole, whereby crystals were precipitated. The crystals were collected by filtration, washed with a sodium carbonate aqueous solution and water, and then dried to obtain 8.8 g of 5-t-butyl-3-formylaminopyrazole. This product was recrystallized from hydrous methanol and found to have a melting point of 204° to 206° C.

Workup

  1. temperatureby heating under reflux conditions
  2. customwhile separating water
  3. distillationby distillation
  4. distillationWhen a calculated amount of water and an excessive amount of formic acid distilled out
  5. additionThe reaction mixture was diluted with water
  6. concentrationconcentrated as whole, whereby crystals
  7. customwere precipitated
  8. filtrationThe crystals were collected by filtration
  9. washwashed with a sodium carbonate aqueous solution and water
  10. customdried

Sources & evidence

ORD record
ord-f3ea8ba54cfc4724a4739d1fd4cab08e
Source dataset
uspto-grants-1985_03
Patent number
US04505739

Reaction notes

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