Triethylamine → HCID 13821934, compound

HRID 1731259Notes

Reaction equation

HRID 1731259 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=O.[C:18](N1C=CN=C1)([N:20]1C=CN=C1)=O.C(N(CC)CC)C.Cl.CN>CN(C=O)C>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:15]([NH:20][CH3:18])=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6364545Methylamine hydrochlorideHCID 13821932HCID 13821932, compound

Product 1

HCID 13821934HCID 13821934, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.2 g of 5-chloro-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid in 150 ml DMF was added 1.1 g of carbonyldiimidazole and the mixture was allowed to stir at room temperature for 20 minutes. One gram of triethylamine and 0.6 g of methylamine hydrochloride were next added to the reaction mixture and the solution was stirred at room temperature for 20 hours. The mixture was poured into ice water and extracted with ethyl acetate. The organic phase was separated and washed with water, dried, and concentrated under vacuum to dryness. The residue was recrystallized from toluene/hexane to afford 650 mg of 5-chloro-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-4-carboxamide. Yield 71%. mp=144°-146° C.

Workup

  1. stirringthe solution was stirred at room temperature for 20 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under vacuum to dryness
  7. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-2146a93422bf46bca1e7ffc1bfcb6795
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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