Diethyl Ether → HCID 178429160, compound

HRID 348016Notes

Reaction equation

HRID 348016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:10]([NH2:13])[NH:11][N:12]=1.[C:21](OCC)(=[O:26])[CH2:22][C:23]([CH3:25])=O.C(OCC)C>C(O)(=O)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:9]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:12][N:11]3[C:21]([OH:26])=[CH:22][C:23]([CH3:25])=[N:13][C:10]=23)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8868Ethyl AcetoacetateHCID 178509105HCID 178509105, compound

Product 1

HCID 178429160HCID 178429160, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-(2-chlorophenyl)-4-(4-chlorophenyl)-2H-pyrazol-3-ylamine (I-3A-1b; 3.00 g, 9.86 mmol) in acetic acid (12 ml) was added ethyl acetoacetate (1.63 ml, 12.8 mmol). The reaction was heated at 100° C. for 16 hours. After cooling to room temperature, the precipitated solid was isolated by vacuum filtration and then repulped from diethyl ether to afford I-3A-4a (1.1 g, 30%) as a colorless solid: +ESI MS (M+1) 370.0; 1H NMR (400 MHz, DMSO-d6) δ 12.12 (s, 1H), 7.45–7.33 (m, 6H), 7.13 (d, J=8.7 Hz, 2H), 5.70 (s, 1H), 2.30 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitated solid was isolated by vacuum filtration
  3. customto afford I-3A-4a (1.1 g, 30%) as a colorless solid

Sources & evidence

ORD record
ord-6ee709fdac5f4ba09afe57ddd2961c14
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

Loading…