Phenylacetic Acid → HCID 11056043, compound

HRID 567794Notes

Reaction equation

HRID 567794 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[NH:4][N:3]=1.[C:14]1([CH2:20][C:21](O)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[NH:4][N:3]=[C:2]([NH:1][C:21](=[O:22])[CH2:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 999Phenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353053-(4-chlorophenyl)-1H-pyrazol-5-amine

Product 1

HCID 11056043HCID 11056043, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-5-(4-chlorophenyl)pyrazole (96.8 mg) and phenylacetic acid (74.9 mg) were dissolved in pyridine (2.5 ml) to which was subsequently added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (143.8 mg), and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate (30 ml), washed with 1 N aqueous potassium hydrogensulfate solution (15 ml×2) and saturated brine (15 ml) and then dried over anhydrous magnesium sulfate. The solvent was distilled away under a reduced pressure, and the resulting residue was crystallized from ethyl acetate and hexane to obtain the title compound (107.8 mg) as white crystals (melting point: 222-224° C.).

Workup

  1. washwashed with 1 N aqueous potassium hydrogensulfate solution (15 ml×2) and saturated brine (15 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under a reduced pressure
  4. customthe resulting residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-3c566ccb873d410aaa174aa972a9fba2
Source dataset
uspto-grants-2001_01
Patent number
US06180653B2

Reaction notes

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