Hydrochloric Acid → HCID 86604920, compound

HRID 1984329Notes

Reaction equation

HRID 1984329 reaction equation
Cl.C([O:4][CH:5](OCC)[C:6]1[CH:7]=[C:8]([C:12]([CH3:24])([CH3:23])[CH2:13][NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([CH3:11])[N:10]=1)C.COC(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH:5]([C:6]1[CH:7]=[C:8]([C:12]([CH3:24])([CH3:23])[CH2:13][NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([CH3:11])[N:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 15413tert-Butyl methyl etherHCID 66958383HCID 66958383, compound

Product 1

HCID 86604920HCID 86604920, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrochloric acid (40 mL of 1 M) was added to a solution of N-[1-(5-diethoxymethyl-2-methyl-2H-pyrazol-3-yl)-1,1-dimethylethyl]benzamide (8.7 g, 24 mmol) in tetrahydrofuran (40 mL), and the reaction was stirred for ten minutes. tert-Butyl methyl ether and 2 M aqueous sodium carbonate (20 mL) were added. The aqueous layer was extracted twice with tert-butyl methyl ether, and the combined organic fractions were dried over magnesium sulfate and filtered. Hexane was added, and the cloudy mixture was stored overnight in the refrigerator. Crystals formed and were isolated in two crops by filtration to provide 5.24 g of N-[1-(5-formyl-2-methyl-2H-pyrazol-3-yl)-1,1-dimethylethyl]benzamide as a white powder, mp 150-151° C.

Workup

  1. extractionThe aqueous layer was extracted twice with tert-butyl methyl ether
  2. dry with materialthe combined organic fractions were dried over magnesium sulfate
  3. filtrationfiltered
  4. additionHexane was added
  5. customCrystals formed
  6. customwere isolated in two crops by filtration

Sources & evidence

ORD record
ord-d713d1c4ae2b488cb88e56ccd71194d0
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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