Acetonitrile → HCID 178434074, compound

HRID 659930Notes

Reaction equation

HRID 659930 reaction equation
[Cl:1][C:2]1[C:17]([O:18][CH2:19][CH2:20][N:21]2[CH:25]=[N:24][N:23]=[N:22]2)=[C:16]([Cl:26])[CH:15]=[CH:14][C:3]=1[C:4]([O:6]C1N(C)N=C(C)C=1)=O.C([N:29]([CH2:32][CH3:33])[CH2:30]C)C.CC(C)([OH:38])C#N.[C:40](#[N:42])[CH3:41]>>[Cl:1][C:2]1[C:17]([O:18][CH2:19][CH2:20][N:21]2[CH:25]=[N:24][N:23]=[N:22]2)=[C:16]([Cl:26])[CH:15]=[CH:14][C:3]=1[C:4]([C:33]1[C:40]([CH3:41])=[N:42][N:29]([CH3:30])[C:32]=1[OH:38])=[O:6]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 592816475-{2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazole

Product 1

HCID 178434074HCID 178434074, compound

Procedure

5-{2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazole (0.65 g) was dissolved in acetonitrile (10 ml), triethylamine (0.33 g) and acetone cyanohydrin (40 mg) were added thereto and the mixture was stirred at room temperature for 12 hours. The solvent was distilled off, acidified by the addition of diluted hydrochloric acid and extracted with ethyl acetate (150 ml). The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. Ethyl acetate was distilled off to obtain objective 4-{2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl}-1,3-dimethyl-5-hydroxy-pyrazole (0.59 g).

Workup

  1. distillationThe solvent was distilled off
  2. additionacidified by the addition of diluted hydrochloric acid
  3. extractionextracted with ethyl acetate (150 ml)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off

Sources & evidence

ORD record
ord-4509f3115030417486da65d02160986c
Source dataset
uspto-grants-2011_12
Patent number
US08084398B2

Reaction notes

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