Triethylamine → HCID 21834439, compound

HRID 1740963Notes

Reaction equation

HRID 1740963 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[CH3:16])[CH:7]=[C:6]([CH3:17])[CH:5]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.C(OCC)(=O)C>[CH3:25][S:26]([O:1][CH2:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[CH3:16])[CH:7]=[C:6]([CH3:17])[CH:5]=1)(=[O:28])=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23506708HCID 23506708, compound

Product 1

HCID 21834439HCID 21834439, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.00 g (8.68 mmol) of 6-(2-hydroxyethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine (from Example 58, Step A) and 1.82 mL (1.32 g, 13.1 mmol) of triethylamine in 20 mL of dichloromethane was cooled to 0° C. and 0.68 mL (1.0 g, 8.8 mmol) of methanesulfonyl chloride was added over 5 min. The mixture was stirred another 25 min at 0° C., diluted with 70 mL of ethyl acetate, and washed with 30 mL each of water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give 2.68 g (100% yield) of 6-(2-methanesulfonyloxyethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine as a viscous pink oil.

Workup

  1. washwashed with 30 mL each of water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. customdecanted
  4. customevaporated

Sources & evidence

ORD record
ord-c5f4110da47c4705a211d9dffdfb1835
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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