Sulfuryl chloride → ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

HRID 1191168Notes

Reaction equation

HRID 1191168 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5])[CH3:2].S(Cl)([Cl:19])(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:10]=1[Cl:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 67412028ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-tert-butyl-2-methyl-pyrazole-3-carboxylic acid ethyl ester (2.10 g, 10.0 mmol) in 25 mL of DCM was added sulfuryl chloride (1.05 ml, 13.0 mmol) slowly under Ar. After stirring at room temperature for 3 h under Ar, the resulting mixture was treated with DCM (30 mL), washed with ice H2O, saturated aqueous NaHCO3 and brine, and dried with Na2SO4. Removal of the solvent under reduced pressure yielded the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 4.40 (q, J=7.2 Hz, 2H), 4.07 (s, 3H), 1.42 (t, J=7.2 Hz, 3H), 1.40 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C11H17ClN2O2: 245.1 (M+H), Measured: 245.1.

Workup

  1. washwashed with ice H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialdried with Na2SO4
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-60a13df573504da0b868f500bf3c0d60
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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