4-Chloroaniline → HCID 14118806, compound

HRID 1693523Notes

Reaction equation

HRID 1693523 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=O.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>S(Cl)(Cl)=O.C(Cl)Cl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:13]([C:3]2[CH:4]=[N:5][N:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:2]=2[NH2:1])=[O:15])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 7468145-Amino-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 14118806HCID 14118806, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid (500 mg, 2.46 mmol) in thionyl chloride (2.0 mL) is stirred at room temperature for about 15 min before it becomes a clear solution. After removal of the solvent, the crude acid chloride is taken in anhydrous DCM (5.0 mL), and transferred dropwise to a solution of 4-chloroaniline (376.7 mg, 2.95 mmol) and TEA (1.03 mL, 7.38 mmol) in anhydrous DCM (5.0 mL) at 0° C. The reaction mixture is allowed to warm up to room temperature in an hour and lots of precipitate is generated. After filtration, the precipitate is washed with water, followed by small amount of DCM, and air-dried to provide crude 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid (4-chloro-phenyl)-amide (506.2 mg, 66% yield) as a white solid product; HPLC-MS calculated for C16H13ClN4O (M+H+) 313.1. Found: 313.0.

Workup

  1. customAfter removal of the solvent
  2. temperatureto warm up to room temperature in an hour
  3. filtrationAfter filtration
  4. washthe precipitate is washed with water
  5. customair-dried

Sources & evidence

ORD record
ord-4776938ab5df4820b125837ada8034eb
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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