Triethylamine → 5-[2-(Methanesulfonyloxy)ethyl]benzofurazan

HRID 1781380Notes

Reaction equation

HRID 1781380 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]([CH:12]=1)=[N:9][O:10][N:11]=2.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH3:20][S:21]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]([CH:12]=1)=[N:9][O:10][N:11]=2)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 150260865-(2-Hydroxyethyl)benzofurazan

Product 1

HCID 151663815-[2-(Methanesulfonyloxy)ethyl]benzofurazanYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

5-(2-Hydroxyethyl)benzofurazan (1.48 g, 9 mmol) was dissolved in dichloromethane (45 ml) and triethylamine (1.88 ml, 1.37 g, 13.5 mmol) was added. The mixture was cooled to -30° C. and methanesulfonyl chloride (0.84 ml, 1.24 g, 10.8 mmol) was added dropwise over 5 min. The mixture was stirred at -30° C. for 15 min. and dichloromethane (100 ml) was added. The mixture was washed with water (100 ml), dried (Na2SO4) and evaporated under reduced pressure to give the benzofurazan as a yellow solid (2.10 g, 96%).

Workup

  1. washThe mixture was washed with water (100 ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-09b8475db80c4c40aa60750fe9e33c66
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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