4-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide → 4-(2-Allyloxybenzamido)-1-methyl-3-n-propyl-pyrazole-5-carboxamide

HRID 1532111Notes

Reaction equation

HRID 1532111 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])[CH:2]=[CH2:3].[NH2:14][C:15]1[C:16]([CH2:24][CH2:25][CH3:26])=[N:17][N:18]([CH3:23])[C:19]=1[C:20]([NH2:22])=[O:21]>ClCCl.N1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:14][C:15]1[C:16]([CH2:24][CH2:25][CH3:26])=[N:17][N:18]([CH3:23])[C:19]=1[C:20]([NH2:22])=[O:21])=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 33380444-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamideHCID 125938922-[(Prop-2-en-1-yl)oxy]benzoyl chloride

Product 1

HCID 536390684-(2-Allyloxybenzamido)-1-methyl-3-n-propyl-pyrazole-5-carboxamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-allyloxybenzoyl chloride (3.93 g, 0.02 mol) in dichloromethane (20 ml) was added dropwise to a stirred, partial solution of 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide (3.64 g, 0.02 mol) in pyridine (50 ml), and the resulting mixture stirred at room temperature overnight in a dry atmosphere. The solvent was evaporated under vacuum and the residue partitioned between dichloromethane (50 ml) and saturated aqueous sodium carbonate solution (50 ml). The organic layer was separated and the aqueous layer exhaustively extracted with further dichloromethane. The combined organic solutions were washed with 2M Hcl (3×30 ml), then brine (1×30 ml), and dried (Na2SO4). After filtration and evaporation under vacuum of the filtrate, the crude product was crystallised from ethyl acetate to give the title compound (4.525 g, 66%), m.p. 132-134° C. Found: C, 63.49; H, 6.42; N, 16.33. C18H22N4O3 requires C, 63.14; H, 6.48; N, 16.36%.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue partitioned between dichloromethane (50 ml) and saturated aqueous sodium carbonate solution (50 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer exhaustively extracted with further dichloromethane
  5. washThe combined organic solutions were washed with 2M Hcl (3×30 ml)
  6. dry with materialbrine (1×30 ml), and dried (Na2SO4)
  7. filtrationAfter filtration and evaporation under vacuum of the filtrate
  8. customthe crude product was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-bdf239cc51f743bdb1497d6fd021e44e
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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