1,2-Dichloroethane → N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}cyclohexanecarboxamide

HRID 1634082Notes

Reaction equation

HRID 1634082 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)CCl.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:23]([C:30]([F:33])([F:32])[F:31])=[N:22]2)=[CH:17][CH:16]=1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[F:33][C:30]([F:31])([F:32])[C:23]1[CH:24]=[C:25]([C:26]([F:27])([F:28])[F:29])[N:21]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:9])=[CH:20][CH:19]=2)[N:22]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 218852-DimethylaminopyridineHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 10158140N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of cyclohexanecarboxylic acid (0.10 g, 0.8 mmol) and EDC (0.077 g, 0.4 mmol) in CH2Cl2 (1.5 mL) was stirred for 15 minutes. 1(4′-Aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.059 g, 0.2 mmol) was added followed by dimethylaminopyridine (0.01 g, 0.1 mmol). After 3 hours the mixture was diluted with CH2Cl2 (50 mL), washed with 10% NaHCO3 (2×50 mL), brine (3×25mL), and dried over anhydrous Na2SO4. Evaporation of the solvent gave the above-named compound as a solid that crystallized from benzene (0.075 g, 92%): mp 178-180° C.; 1H NMR (CDCl3) δ 1.35 (3H, m), 1.66 (2H, m), 1.75 (1H, m), 1.85 (2H, m), 2.0 (2H, m), 2.3 (1H, m), 7.08 (1H, s), 7.45 (1H, d, J=8.5 Hz), 7.75 (2H, d, J=8.5 Hz).

Workup

  1. washwashed with 10% NaHCO3 (2×50 mL), brine (3×25mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4ad2f92fc19141c88a5b7543995421ed
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…