Methanesulfonyl chloride → HCID 15077739, compound

HRID 2380283Notes

Reaction equation

HRID 2380283 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH2:9])=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[N:5]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl.C(N(CC)CC)C>[CH3:15][S:16]([O:1][CH2:2][CH2:3][N:4]1[C:8]([NH2:9])=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[N:5]1)(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 429881Ethyl 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 15077739HCID 15077739, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-4-ethoxycarbonyl-5-aminopyrazole (200 g) in a mixture of methylene chloride (2 l) and triethylamine (210 ml) was added dropwise methanesulfonyl chloride (85.5 ml) under ice-cooling. The mixture was stirred for 1 hour at 3°-5° C. The reaction mixture was poured into ice-water (700 ml). The separated organic layer was washed with 1N hydrochloric acid and water, and dried over magnesium sulfate. The solvent was evaporated to give 1-(2-methylsulfonyloxyethyl)-4-ethoxycarbonyl-5-aminopyrazole (270.8 g) as crystals.

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with 1N hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-abde1cb5470a442698c41ac1cbb3cfa2
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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