Hydrochloric Acid → HCID 178502623, compound

HRID 2304892Notes

Reaction equation

HRID 2304892 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][N:9]=[C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11]1.[N:19](OC(C)(C)C)=[O:20].Cl>C(O)(C)(C)C>[CH3:7][O:8][N:9]=[C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]1=[N:19][OH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 23665647Potassium tert-butoxideHCID 542716163(2H)-Benzofuranone, O-methyloxime

Product 1

HCID 178502623HCID 178502623, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

3.92 g (0.035 mol) of potassium tert-butoxide are dissolved in 40 ml of tert-butanol. A solution of 5.7 g (0.035 mol) of benzofuran-3-one O-methyl-oxime and 7.2 g (0.07 mol) of tert-butyl nitrite in 10 ml of tert-butanol is added to this solution. The mixture is stirred without cooling for two hours and then admixed with 20 ml of 2N aqueous hydrochloric acid. The crystalline product is filtered off, washed repeatedly with water and dried in a desiccator. 3.19 g (47.1% of theory) of benzofuran-2,3-dione 3-(O-methyl-oxime) 2-oxime are obtained as a mixture of two stereoisomers comprising 86.33% of isomer A and 12.98% of isomer B (HPLC).

Workup

  1. temperaturewithout cooling for two hours
  2. filtrationThe crystalline product is filtered off
  3. washwashed repeatedly with water
  4. customdried in a desiccator

Sources & evidence

ORD record
ord-c1c4fd4e00d24d6288fb1108f3a1b30c
Source dataset
uspto-grants-2002_08
Patent number
US06437153B1

Reaction notes

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