Hydrochloric Acid → N-allyloxy-3,5-dichloro-1-methylpyrazole-4-carboxylic acid amide

HRID 225418Notes

Reaction equation

HRID 225418 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:12]([C:13]([NH:15][OH:16])=[O:14])=[C:11]([Cl:17])[N:10]([CH3:18])[N:9]=1.[CH2:19](Br)[CH:20]=[CH2:21].Cl>O.C1(C)C=CC=CC=1>[CH2:21]([O:16][NH:15][C:13]([C:12]1[C:8]([Cl:7])=[N:9][N:10]([CH3:18])[C:11]=1[Cl:17])=[O:14])[CH:20]=[CH2:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 57752427HCID 57752427, compound

Product 1

HCID 57752428N-allyloxy-3,5-dichloro-1-methylpyrazole-4-carboxylic acid amideYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In a solution of potassium carbonate (15.8 g, 114 mmol) in water (60 ml), a solution of 3,5-dichloro-1-methylpyrazole-4-carbohydroxamic acid (20.0 g, 95.2 mmol) and allyl bromide (13.8 g, 114 mmol) in toluene (60 ml) was added, and stirred at 50° C. for 3 hours. After cooling to room temperature, the mixture was adjusted to pH 1 by adding 35% hydrochloric acid, precipitated solid was filtered off, washed with water and toluene in that order, and dried to obtain the aimed product (17.2 g). Melting point 96-97° C. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.84 (s, 3H), 4.51 (d, J=6.3 Hz, 2H), 5.3-5.46 (m, 2H), 5.94-6.13 (m, 1H), 8.80 (brs, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customprecipitated solid
  3. filtrationwas filtered off
  4. washwashed with water and toluene in that order
  5. customdried

Sources & evidence

ORD record
ord-88d79534543f45ca8f26511391ec5734
Source dataset
uspto-grants-2009_07
Patent number
US07557067B2

Reaction notes

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