Dimethylamine, hydrochloride → HCID 19886178, compound

HRID 654783Notes

Reaction equation

HRID 654783 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:21]([OH:23])=O)=[N:9]2)=[CH:4][CH:3]=1.[C:24](N1C=CN=C1)([N:26]1C=CN=[CH:27]1)=O.Cl.CNC.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:21]([N:26]([CH3:27])[CH3:24])=[O:23])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 10782496HCID 10782496, compound

Product 1

HCID 19886178HCID 19886178, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazole-3-carboxylic acid (3 g) and 1,1'-carbonyldiimidazole (1.6 g) in tetrahydrofuran (39 ml) was refluxed for 1 hour. Dimethylamine hydrochloride (1.04 g) and potassium carbonate (1.33 g) were added, and the resulting mixture was stirred and refluxed for 3 hours. The mixture was diluted with ethyl acetate, washed with water, an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water, successively, dried and concentrated to give a pale brown oil of 1-(4-fluorophenyl)-N,N-dimethyl-5-[4-(methylthio)phenyl]pyrazole-3-carboxamide (2.6 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturerefluxed for 3 hours
  3. washwashed with water
  4. dry with materialan aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water, successively, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-827825e64ef0441b9ad0da618b8977d3
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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