Chlorotrimethylsilane → HCID 68509351, compound

HRID 2400532Notes

Reaction equation

HRID 2400532 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[C:4]=1[CH3:11])[CH3:2].[Cl:12][Si](C)(C)[CH3:14]>CO>[ClH:12].[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([C:8]([O:10][CH3:14])=[O:9])[C:4]=1[CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 31596385-Ethyl-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 68509351HCID 68509351, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mechanically stirred suspension of 5-ethyl-4-methyl-1H-pyrazole-3-carboxylic acid (1.0 g, 6.49 mmol) in dry methanol (30 mL) was added chlorotrimethylsilane (2.5 mL, 19.5 mmol). The reaction mixture was heated at reflux over night. After being cooled to rt, the solvent was removed in vacuo, and the residue was stirred in diethyl ether (20 mL) for 1 h. After filtration and vacuum drying the title compound was obtained as white crystals (832 mg, 63%): 1H NMR (400 MHz, CDCl3) δ 10.55 (broad, 1H), 4.00 (s, 3H), 2.91 (quart, 2H), 2.32 (s, 3H), 1.35 (t, 3H); ES-MS m/z 169 (MH)+; HPLC RT (Method F) 1.52 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux over night
  3. customthe solvent was removed in vacuo
  4. filtrationAfter filtration and vacuum
  5. dry with materialdrying the title compound

Sources & evidence

ORD record
ord-dc22f6aec5d44ffebf4cb8fd80b5ef2d
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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