Hydrochloric Acid → HCID 178502623, compound

HRID 636843Notes

Reaction equation

HRID 636843 reaction equation
C([O:5][N:6]=O)(C)(C)C.Cl.[CH3:9][O:10][N:11]=[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH2:13]1>C(OCC)(=O)C>[CH3:9][O:10][N:11]=[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][C:13]1=[N:6][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 542716163(2H)-Benzofuranone, O-methyloxime

Product 1

HCID 178502623HCID 178502623, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2 g (0.019 mol) of tert-butylnitrite are added dropwise to 30 ml of ethyl acetate saturated with dry hydrogen chloride at −10° C. and the mixture is stirred at this temperature for 15 minutes. 1.6 g (0.0098 mol) of benzofuran-3-one O-methyl oxime dissolved in 5 ml of ethyl acetate are then added at −10° C., the temperature is allowed to rise to 0° C. and the mixture is stirred at this temperature for 30 minutes. The product which has crystallized out is filtered off and 1.08 g of crystalline benzofuran-2,3-dione 3-(O-methyl oxime) 2-oxime are obtained as mixture of two stereoisomers which, according to the HPLC analysis, comprises isomer B to the extent of 54.7% (56% of theory) and isomer A to the extent of 42.9%.

Workup

  1. additionare then added at −10° C.
  2. customto rise to 0° C.
  3. stirringthe mixture is stirred at this temperature for 30 minutes
  4. customThe product which has crystallized out
  5. filtrationis filtered off

Sources & evidence

ORD record
ord-be663ecf54264d2aac58264a3b713890
Source dataset
uspto-grants-2001_02
Patent number
US06194590B1

Reaction notes

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