Ethyl Acetate → 5-Amino-1-(2-tolyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582012Notes

Reaction equation

HRID 582012 reaction equation
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[C:18]1([CH3:26])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][NH2:25].[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:2][C:1]1[N:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH3:26])[N:25]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 538751495-Amino-1-(2-tolyl)-3-(4-tolyl)pyrazole-4-carboxamideYield 4.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (464 mg, 2.0 mmol), 2-tolylhydrazine hydrochloride (350 mg, 2.2 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 75% ethyl acetate in hexane) to give the title compound as a yellow solid (30 mg) m.p. 133-135°. δH (CDCl3) 7.52 (2H, d, J 8.1 Hz), 7.38 (4H, m), 7.28 (2H, d, J 7.4 Hz), 5.40 (4H, m), 2.40 (3H, s) and 2.23 (3H, s).

Sources & evidence

ORD record
ord-d8cc42b5c4a14489adec7ee652103db8
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

Loading…