Hydrochloric Acid → HCID 136175584, compound

HRID 2406118Notes

Reaction equation

HRID 2406118 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26](OC)=O)[CH:22]=[CH:23][CH:24]=1.[H-].[Na+].Cl.[Cl-].[Na+]>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:25][C:26]1[NH:17][C:15](=[O:16])[C:3]2[CH:4]=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=3[CH3:14])[C:2]=2[N:1]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 2733544Methyl 2-(3-chlorophenyl)acetateHCID 121505625-amino-1-(2,3-dimethylphenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 136175584HCID 136175584, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.1 g (0.43 mmol) of 5-amino-1-(2,3-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 17A) is dissolved under argon in 6 ml of absolute ethanol and 0.24 g (1.3 mmol) of methyl 3-chlorophenylacetate and 0.17 g (4.34 mmol) of 60% sodium hydride (suspension in mineral oil) are added. The reaction mixture is heated to reflux overnight. Cooling to room temperature is followed by acidification with concentrated hydrochloric acid. The mixture of sodium chloride and the product precipitated thereby is filtered off and washed several times with water and diethyl ether. Drying under high vacuum results in 97 mg (61% of theory) of the product as colourless solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe product precipitated
  4. filtrationthereby is filtered off
  5. washwashed several times with water and diethyl ether
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-deaf8304816a4c1eabe58aab4949f717
Source dataset
uspto-grants-2014_08
Patent number
US08809348B2

Reaction notes

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