Thionyl Chloride → HCID 10805016, compound

HRID 1251009Notes

Reaction equation

HRID 1251009 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](O)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.S(Cl)([Cl:24])=O>>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15]([Cl:24])=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10732464HCID 10732464, compound

Product 1

HCID 10805016HCID 10805016, compound

Procedure

A mixture of 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carboxylic acid (12) (500 mg, 1.70 mmol) in thionyl chloride (twice distilled over triphenyl phosphite) (25 mL) was heated at reflux for 20 hours. The reaction mixture was concentrated to an off-white solid which was purified by elution through a flash column (4:1 hexanes:ethyl acetate), 510 mg (96%), mp 162-164° C.; 1H NMR (CDCl3): δ 8.35 (s, 1H), 4.15 (s, 3H), 4.03 (s, 3H), 2.55 (s, 3H); MS: m/z 312 (M+H).

Workup

  1. distillationtwice distilled over triphenyl phosphite) (25 mL)
  2. temperaturewas heated
  3. temperatureat reflux for 20 hours
  4. concentrationThe reaction mixture was concentrated to an off-white solid which
  5. customwas purified by elution through a flash column (4:1 hexanes:ethyl acetate), 510 mg (96%), mp 162-164° C.

Sources & evidence

ORD record
ord-4d2040eb5a8d465fa9f6a14d54262b5e
Source dataset
uspto-grants-2002_01
Patent number
US06340758B1

Reaction notes

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