Hydrochloric Acid → HCID 57752415, compound

HRID 225420Notes

Reaction equation

HRID 225420 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([S:14][C:15]1[N:19]([CH3:20])[N:18]=[CH:17][C:16]=1[C:21]([NH:23][OH:24])=[O:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:25](Br)[CH:26]=[CH2:27].Cl>O.C1(C)C=CC=CC=1>[CH2:27]([O:24][NH:23][C:21]([C:16]1[CH:17]=[N:18][N:19]([CH3:20])[C:15]=1[S:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:22])[CH:26]=[CH2:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 57752439HCID 57752439, compound

Product 1

HCID 57752415HCID 57752415, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In a solution of potassium carbonate (1.3 g, 9.4 mmol) in water (10 ml), a solution of 5-benzylthio-1-methylpyrazole-4-carbohydroxamic acid (2.0 g, 7.6 mmol) and allyl bromide (1.1 g, 9.1 mmol) in toluene (10 ml) were added, and stirred at 50° C. for 4 hours. After cooling to room temperature, the mixture was adjusted to pH 1 by adding 35% hydrochloric acid and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the aimed product (1.9 g). Oily substance. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.42 (s, 3H), 3.95 (s, 2H), 4.49 (d, J=6.3 Hz, 2H), 5.33-5.43 (m, 2H), 6.00-6.16 (m, 1H), 6.93-7.00 (m, 2H), 7.21-7.30 (m, 3H), 8.08 (s, 1H), 9.68 (brs, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe resulting ethyl acetate solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-319453a6fb2f45b398cd89fed45d81d0
Source dataset
uspto-grants-2009_07
Patent number
US07557067B2

Reaction notes

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