Nitrosylsulfuric acid → HCID 58062852, compound

HRID 1950934Notes

Reaction equation

HRID 1950934 reaction equation
N(OS(=O)(=O)O)=[O:2].[CH2:8]([O:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([O:29][CH3:30])[C:17]=1[C:18](N)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.ClCCl>[CH2:8]([O:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([O:29][CH3:30])[C:17]=1[C:18]([OH:2])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 82157Nitrosylsulfuric acidHCID 58062859HCID 58062859, compound

Product 1

HCID 58062852HCID 58062852, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.81 g (12.81 mmol) nitrosylsulfuric acid in 1.5 ml water at 0° C. under nitrogen, was added dropwise a suspension of 463 mg (1.423 mmol) 2-benzyloxy-6-methoxy-4-trifluoromethyl-benzamide in 2.9 ml dichloromethane. The reaction mixture was stirred at 0° C. for 4 hours. The reaction mixture was poured over ice and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude solid was purified with flash column chromatography on silica (20 g) eluting with a gradient formed from n-heptane and ethyl acetate (0%=>100% in 15 minutes) to provide 431 mg (y: 64.9% yield) of the title compound as a white solid. MS (m/e): 325.1 (M−H)

Workup

  1. additionThe reaction mixture was poured over ice
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude solid was purified with flash column chromatography on silica (20 g)
  7. washeluting with a gradient
  8. customformed from n-heptane and ethyl acetate (0%=>100% in 15 minutes)

Sources & evidence

ORD record
ord-5c79695fa41c42e59abf23cf12e3ee71
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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