Hydrochloric Acid → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxy-amide

HRID 2381252Notes

Reaction equation

HRID 2381252 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH:22]([NH:24][OH:25])[CH3:23].C(N(CC)CC)C.Cl>ClCCl>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH:22]([N:24]([OH:25])[C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 246151N-[2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

Product 1

HCID 584436843-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxy-amideYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (2.10 g; 11.0 mmol) in dichloromethane (5 ml) was added dropwise to a stirred suspension of N-[2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxylamine (2.0 g; 9.10 mmol), prepared as described in example P17, triethylamine (3.10 ml; 22 mmol) in dichloromethane (15 ml) at 0° C. The reaction mixture was stirred over night at ambient temperature. The reaction mixture was poured onto 1M HCl (50 ml), extracted with dichloromethane (3×20 ml) and then dried over Na2SO4. After removal of the solvent the residue (5.08 g) was purified by flash chromatography over silica gel (eluant: c-hexane/ethyl acetate 7:3). 1.51 g (43.8% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxy-amide (compound 1.028) was obtained in form of a white solid (m.p. 162-167° C.).

Workup

  1. customprepared
  2. extractionextracted with dichloromethane (3×20 ml)
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent the residue (5.08 g)
  5. customwas purified by flash chromatography over silica gel (eluant: c-hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-74b20e59225741f7a0d0556e52f86c88
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

Loading…