Ammonium Chloride → HCID 67212485, compound

HRID 1671335Notes

Reaction equation

HRID 1671335 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:24][CH3:25])=[N:8][NH:9][C:10]=1[O:11][CH:12]([CH3:23])[C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=O)=[O:5])[CH3:2].[NH4+].[Cl-]>ClCCCl.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:24][CH3:25])=[N:8][N:9]2[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])=[C:12]([CH3:23])[O:11][C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 136376636HCID 136376636, compound

Product 1

HCID 67212485HCID 67212485, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution 5-[2-(2,4-dichloro-phenyl)-1-methyl-2-oxo-ethoxy]-3-ethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.48 g, 6.44 mmol) in 1,2-dichloroethane (40 ml) at RT is added TiCl4 (0.86 ml, 7.73 mmol). The reaction mixture is heated to 80° C. for 2 hrs. On cooling, the mixture is poured into a stirred sat. aq. NH4Cl (150 ml), (stirring continued for 5-10 mins following addition). Celite® (filter material) is added to this mixture and then filtered through a Celite® bed. The filter-cake is washed with EtOAc (30 ml) and the filtrate is extracted with EtOAc (approx. 90 ml). The combined organics are washed with 2N Na2CO3 (30 ml), brine and dried with sodium sulphate. On evaporation the resultant solid residue is triturated in 3/1 v/v iso-hexane/diethyl ether (15 ml) at RT for ½ h; the solid is filtered and dried in vacuo to give the title compound as a white solid yield: MS: m/z 367.20 [M+H]+

Workup

  1. temperatureOn cooling
  2. filtrationCelite® (filter material)
  3. additionis added to this mixture
  4. filtrationfiltered through a Celite® bed
  5. washThe filter-cake is washed with EtOAc (30 ml)
  6. extractionthe filtrate is extracted with EtOAc (approx. 90 ml)
  7. washThe combined organics are washed with 2N Na2CO3 (30 ml), brine
  8. dry with materialdried with sodium sulphate
  9. customOn evaporation the resultant solid residue
  10. customis triturated in 3/1 v/v iso-hexane/diethyl ether (15 ml) at RT for ½ h
  11. filtrationthe solid is filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-6e43edb4f2fb45fd9fe7c78deb8ac450
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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