Triethylamine → methanesulfonic acid 1-methyl-1H-pyrazol-4-ylmethyl ester

HRID 246342

Reaction equation

HRID 246342 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][OH:8])[CH:4]=[N:3]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][O:8][S:17]([CH3:16])(=[O:19])=[O:18])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11961423(1-methyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 86677974methanesulfonic acid 1-methyl-1H-pyrazol-4-ylmethyl esterYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a partial suspension of (1-methyl-1H-pyrazol-4-yl)methanol (75 mg, 0.67 mmol) in CH2Cl2 (4 mL) at 0° C. was added triethylamine (0.19 mL, 1.34 mmol) followed by methanesulfonyl chloride (57 μL, 0.74 mmol). The cloudy reaction mixture was stirred at 0° C. for 1 h then quenched with water and extracted with CH2Cl2. The organics were dried over MgSO4 and concentrated to give 110 mg of methanesulfonic acid 1-methyl-1H-pyrazol-4-ylmethyl ester a colorless oil which was used without further purification.

Workup

  1. customThe cloudy reaction mixture
  2. customthen quenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-970c8880cb2a42609aec577bb9388b8c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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