Acetonitrile → HCID 178496176, compound

HRID 1642013Notes

Reaction equation

CN1C(O[C:8](=[O:25])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:11]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C:10]=2[CH3:24])=CC=N1.C([N:28]([CH2:31][CH3:32])[CH2:29]C)C.CC(C)([OH:37])C#N.[C:39](#[N:41])C>>[CH3:23][O:22][CH2:21][CH2:20][O:19][C:11]1[C:10]([CH3:24])=[C:9]([CH:14]=[CH:13][C:12]=1[S:15]([CH3:18])(=[O:16])=[O:17])[C:8]([C:32]1[CH:39]=[N:41][N:28]([CH3:29])[C:31]=1[OH:37])=[O:25]

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 6406Acetone Cyanohydrin

HCID 8471Triethylamine

HCID 667559103-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid 1-methyl-1H-pyrazol-5-yl ester

Product 1

HCID 178496176HCID 178496176, compound

Procedure

3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid 1-methyl-1H-pyrazol-5-yl ester (7.8 g) was dissolved in acetonitrile (100 mL), and triethylamine (7.9 mL) and acetone cyanohydrin (0.87 mL) were added at room temperature. After stirring for 6 hours, the solvent was distilled off under reduced pressure. To the residue, ethyl acetate (100 mL) was added, followed by washing sequentially with 1N hydrochloric acid (50 mL), water and saturated brine, and drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with hexane to obtain 4-(3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl)-1-methyl-1H-pyrazol-5-ol (4.2 g).

Workup

distillationthe solvent was distilled off under reduced pressure
additionTo the residue, ethyl acetate (100 mL) was added
washby washing sequentially with 1N hydrochloric acid (50 mL), water and saturated brine
dry with materialdrying over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
washthe residue was washed with hexane

Sources & evidence

ORD record: ord-362ea7becb62469ea53c78980f8d2cb3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119569B2

Reaction notes

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