Hydroxylamine → HCID 67217531, compound

HRID 1505281Notes

Reaction equation

HRID 1505281 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[N:7]=[C:8]([CH:10]=O)[CH:9]=1)=[O:4].[NH2:13][OH:14].ClN1C(=O)CCC1=O.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[CH:25]=1>C(O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[N:7]=[C:8]([C:10]2[CH2:31][C:30]([C:28]3[CH:29]=[C:24]([Cl:23])[CH:25]=[C:26]([Cl:36])[CH:27]=3)([C:32]([F:33])([F:34])[F:35])[O:14][N:13]=2)[CH:9]=1)=[O:4]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 58498000Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 67217531HCID 67217531, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 5-Formyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (210 mg) in ethanol (10 mL), was added aqueous NH2OH (50% in water, 0.10 mL). The solution was stirred at room temperature for 4 hours then was concentrated to give a white solid which was then dissolved in dimethylformamide (4 mL). To this solution was added N-chlorosuccinimide (180 mg). The solution was stirred at room temperature for 4 hours. This solution was slowly added to a solution of 1,3-Dichloro-5-(1-trifluoromethyl-vinyl)-benzene (750 mg) (prepared according to WO 2005/085216) in dimethylformamide (6 mL). When the addition was completed, triethylamine (0.2 mL) was added. The solution was stirred at room temperature for 4 hours then the reaction was then quenched by addition of water. After extraction with diethyl ether, the organic phase was separated, dried over magnesium sulfate and concentrated to give an orange oil. The residue was purified by chromatography over silica (heptane/diethyl ether; 1/0 to 7/3) to give 300 mg of 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as a white solid. 1H-NMR (CDCl3, 400 MHz): 7.48 (m, 2H), 7.39-7.38 (m, 1H), 7.23 (s, 1H), 4.17 (s, 3H), 4.14 (d, 1H), 3.89 (s, 3H), 3.75 (d, 1H).

Workup

  1. concentrationthen was concentrated
  2. customto give a white solid which
  3. stirringThe solution was stirred at room temperature for 4 hours
  4. additionWhen the addition
  5. stirringThe solution was stirred at room temperature for 4 hours
  6. customthe reaction was then quenched by addition of water
  7. extractionAfter extraction with diethyl ether
  8. customthe organic phase was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give an orange oil
  12. customThe residue was purified by chromatography over silica (heptane/diethyl ether; 1/0 to 7/3)

Sources & evidence

ORD record
ord-a4fa89458aa5455f863de37cecd189c2
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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