Dichloromethane → HCID 86659919, compound

HRID 2038445Notes

Reaction equation

HRID 2038445 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:11][OH:12])[C:3](=[O:13])[O:2]1.Cl[CH2:15][Cl:16].S(Cl)(Cl)=O>CO.CC(OC)(C)C>[CH3:1][O:2][C:3](=[O:13])[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:15][Cl:16])=[N:11][OH:12]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 73443586HCID 73443586, compound

Product 1

HCID 86659919HCID 86659919, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of isochroman-3,4-dione 4-oxime (98% pure, 3.5 g, 0.02 mol) in methanol (35 g) and dichlormethane (32 g) was added dropwise at 20-30° C. thionyl chloride (24.0 g, 0.2 mol). The resulting mixture was stirred at ambient temperature for 3 d. The reaction was monitored by HPLC. After completion of the reaction, the mixture was concentrated in vacuo and a crude residue was obtained (5.5 g). A part of this residue (5.1 g) was dissolved in MTBE and was washed with water. The mixture was concentrated and the resulting residue was purified by silica column chromatography by yield (2-chloromethyl-phenyl)-hydroxyimino-acetic acid methyl ester as a colorless solid (3.4

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. customa crude residue was obtained (5.5 g)
  4. washwas washed with water
  5. concentrationThe mixture was concentrated
  6. customthe resulting residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-844661f778dc4730b15d14db45322966
Source dataset
uspto-grants-2013_11
Patent number
US08575366B2

Reaction notes

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