Water → HCID 21083548, compound

HRID 347662Notes

Reaction equation

HRID 347662 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[N:23][NH:24][CH:25]=1.O>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:25]=[N:24][N:23]([C:2]([O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:3])[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 821294-Nitrophenyl chloroformate2×HCID 133207394-(2-Chlorophenyl)-1H-pyrazole

Product 1

HCID 21083548HCID 21083548, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrophenyl chloroformate (2.3 g, 11.5 mmol) and 4-(2-chlorophenyl)-1H-pyrazole (2.0 g, 11.0 mmol) are dissolved in 30 mL CH2Cl2 and cooled to 0° C. TEA (1.7 mL, 12.0 mmol) is added, and the reaction is allowed to warm to RT. After 30 min, additional 4-nitrophenyl chloroformate (0.25 g) and TEA are added. After 1 h, water is added. The mixture is extracted with CH2Cl2, dried (MgSO4), filtered and concentrated to give a solid. The solid is triturated with hexanes, filtered and dried to provide 1.7 g (45%) of the crude 4-nitrophenyl 4-(2-chlorophenyl)-1H-pyrazole-1-carboxylate.

Workup

  1. temperatureto warm to RT
  2. waitAfter 1 h
  3. extractionThe mixture is extracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid is triturated with hexanes
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-6fd57152a0194f69be0c841842acf8b7
Source dataset
uspto-grants-2007_02
Patent number
US07176198B2

Reaction notes

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