Hydrochloric Acid → HCID 178502623, compound

HRID 2304893Notes

Reaction equation

HRID 2304893 reaction equation
[N:1](OC(C)(C)C)=[O:2].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:1][OH:2]

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×

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. additionare then added
  2. stirringthe mixture is stirred at this temperature for 30 minutes
  3. filtrationThe crystalline product is filtered off

Sources & evidence

ORD record
ord-1bfa50b3eb93492db4f05bb57c7d2907
Source dataset
uspto-grants-2002_08
Patent number
US06437153B1

Reaction notes

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