Acetone Cyanohydrin → HCID 178422700, compound

HRID 1066704Notes

Reaction equation

HRID 1066704 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:12])[C:3]=1[C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1.S(Cl)(Cl)=O.Cl.[CH3:24][N:25]1[C:29]([OH:30])=[CH:28][CH:27]=[N:26]1.CC(C)(O)C#N>C1C=CC=CC=1.N1C=CC=CC=1.C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([C:27]2[CH:28]=[C:29]([OH:30])[N:25]([CH3:24])[N:26]=2)=[O:8])=[C:4]([CH3:12])[C:3]=1[C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1

Participants

9

Reactant 4

HCID 6406Acetone CyanohydrinHCID 24386Thionyl ChlorideHCID 97958614,5-Dichloro-2-methyl-3-(3-methylisoxazole-5-yl)benzoic acidHCID 178478934HCID 178478934, compound

Product 1

HCID 178422700HCID 178422700, compound

Reagents, catalysts & solvents 4

HCID 1049PyridineCatalystHCID 241BenzeneSolventHCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

4,5-Dichloro-2-methyl-3-(3-methylisoxazole-5-yl)benzoic acid in an amount of 0.35 g (1.2 mmol) was dissolved in 10 ml benzene, and the resulting solution was then added with thionyl chloride in an amount of 0.18 g (1.5 mmol) and one drop of pyridine and was stirred for 2 hours under heating and reflux. After distillating out the solvent from the reacted mixture under reduced pressure, the residue was dissolved in 3 ml chloroform and the resulting solution was added dropwise into a mixture of 1-methyl-5-hydroxypyrazole hydrochloride in an amount of 0. 19 g (1.4 mmol), 4 ml chloroform and triethyl amine in an amount of 0.26 g (2.6 mmol) while cooling with ice. After stirring the mixture for 30 minutes at an ambient temperature, the mixture was further added with acetone cyanohydrine in an amount of 0.03 g (0.4 mmol) and triethyl amine in an amount of 0.23 g (2.3 mmol) and was further stirred overnight at an ambient temperature. The reacted solution was washed with 1N-hydrochloric acid and then with saturated brine, then dried with anhydrous magnesium sulfate, and the solvent therein was distillated out. The obtained crystals were washed with methanol to obtain the objective compound in an amount of 0.33 g in crystalline form. Mp. 171-173° C.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. stirringAfter stirring the mixture for 30 minutes at an ambient temperature
  4. waitwas further stirred overnight at an ambient temperature
  5. washThe reacted solution was washed with 1N-hydrochloric acid
  6. dry with materialwith saturated brine, then dried with anhydrous magnesium sulfate
  7. washThe obtained crystals were washed with methanol
  8. customto obtain the objective compound in an amount of 0.33 g in crystalline form

Sources & evidence

ORD record
ord-dc64ea1a0de14bc9ac74c7c2fe80447d
Source dataset
uspto-grants-2001_06
Patent number
US06245716B1

Reaction notes

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