Triethylamine → 5-(Methanesulfonyloxymethyl)benzofurazan

HRID 1195671Notes

Reaction equation

HRID 1195671 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:2]=12.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[C:3]([CH:6]=1)=[N:4][O:5][N:1]=2)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27762972,1,3-Benzoxadiazol-5-ylmethanol

Product 1

HCID 190452515-(Methanesulfonyloxymethyl)benzofurazanYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

5-Benzofurazanmethanol (0.6 g, 4 mmol) and triethylamine (0.84 mmol, 0.61 g, 6 mmol) were dissolved in dichloromethane (20 ml) and cooled to -20° C. Methanesulfonyl chloride (0.37 ml, 0.55 g, 4.8 mmol) was added dropwise and the mixture was stirred at -20° C. for 20 minutes, diluted with dichloromethane (30 ml), washed with water (30 ml), dried (Na2SO4), and evaporated under reduced pressure to give the benzofurazan as a white solid (0.91 g, 99%).

Workup

  1. washwashed with water (30 ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e4cf4ba955264aa487a34d04efd49bbb
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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