Hydrochloric Acid → HCID 178488023, compound

HRID 659825Notes

Reaction equation

HRID 659825 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:13])[C:7](O)=[N:6]2.O=S(Cl)[Cl:17].Cl>CN(C=O)C>[Cl:17][C:7]1[C:8]([OH:13])=[N:9][C:10]2[C:5]([N:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 178488026HCID 178488026, compound

Product 1

HCID 178488023HCID 178488023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution (1.53 M) of 6-methoxyquinoxaline-2,3-diol in DMF was treated with SOCl2 (1 eq) and heated at 110° C. After 1.5 h, the reaction mixture was cooled and poured into aqueous HCl (1 N). The resulting precipitate was filtered and washed with H2O and Et2O. The dried solid contained predominantly the title compound as a mixture with 6-methoxyquinoxaline-2,3-diol and 2,3-dichloro-6-methoxyquinoxaline. This material was used directly in the subsequent step. MS (ES+) m/z 211 (M+H)+

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O and Et2O

Sources & evidence

ORD record
ord-f68c3efe021647389423858c30b425de
Source dataset
uspto-grants-2011_12
Patent number
US08080654B2

Reaction notes

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