Triethylamine → [1-(4-Chloromethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

HRID 1631927Notes

Reaction equation

HRID 1631927 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:6]([CH3:20])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][CH:13]=2)[C:9]=1[CH3:10].C(N(CC)CC)C.CS([Cl:33])(=O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:6]([CH3:20])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][Cl:33])=[CH:14][CH:13]=2)[C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66707588[1-(4-Hydroxymethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester2×

Product 1

HCID 66707535[1-(4-Chloromethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(4-Hydroxymethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 16.1.1, 4.8 g, 16.7 mmol) was dissolved in 60 ml dichloromethane. Triethylamine (3.5 ml, 25 mmol) was added, followed by dropwise addition of methanesulfonyl chloride (1.29 ml, 16.7 mmol). After 12 h at room temperature, the mixture was washed with water, aqueous KHSO4 solution, water, aqueous NaHCO3 solution and with water. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure.

Workup

  1. washthe mixture was washed with water, aqueous KHSO4 solution, water, aqueous NaHCO3 solution and with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b126cfe40b1743b98c3e828f09d7e931
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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