Triethylamine → HCID 57899277, compound

HRID 1802793Notes

Reaction equation

HRID 1802793 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:17])[N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([CH3:10])[C:8]=1[CH3:9].C(N(CC)CC)C.[CH3:25][S:26]([Cl:29])(=[O:28])=[O:27].[Cl-].[NH4+]>ClCCl>[CH3:10][N:7]1[C:8]([CH3:9])=[C:4]([CH2:3][CH2:2][O:1][S:26]([CH3:25])(=[O:28])=[O:27])[C:5](=[O:17])[N:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:29][CH2:2][CH2:3][C:4]1[C:5](=[O:17])[N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([CH3:10])[C:8]=1[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 54516649HCID 54516649, compound

Product 2

HCID 57899277HCID 57899277, compoundHCID 57899299HCID 57899299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (700 mg, 3.01 mmol), triethylamine (0.84 mL, 6.0 mmol), and methyl sulfonyl chloride (0.28 mL, 3.6 mmol) in dichloromethane (5.0 mL) was stirred at room temperature for 4 h. The reaction mixture was treated with saturated ammonium chloride and extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via silica gel column chromatography provided methanesulfonic acid 2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-ethyl ester (384 mg) and 4-(2-chloro-ethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (310 mg) in 41% combined yield. LCMS 311.3 (M+1) and LCMS 251.3 (M+1), respectively.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel column chromatography

Sources & evidence

ORD record
ord-5571e4a7292446ea885b6c9d8667d744
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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