Hydrochloric Acid → HCID 178502623, compound

HRID 1250019Notes

Reaction equation

HRID 1250019 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-bd13bb22a4a448178351368ef6bad0c4
Source dataset
uspto-grants-2002_01
Patent number
US06335454B1

Reaction notes

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