Formaldehyde → HCID 22614842, compound

HRID 842683Notes

Reaction equation

HRID 842683 reaction equation
[Cl:1][C:2]1[C:3]([N:17]2[CH:21]=[N:20][N:19]=[C:18]2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[CH2:28]=O.Cl.[CH3:31][NH:32][CH3:33]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:17]2[C:18]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:19][N:20]=[C:21]2[CH2:31][N:32]([CH3:28])[CH3:33])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 22614854HCID 22614854, compound

Product 1

HCID 22614842HCID 22614842, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6,7-dichloro-2,3-dimethoxy-5-[3-(3-pyridyl)-4H-1,2,4-triazol-4-yl]quinoxaline (Preparation 98, 101 mg, 0.25 mmol), paraformaldehyde (15 mg, 0.5 mmol) and dimethylamine hydrochloride (22 mg, 0.27 mmol) in acetic acid (5 mL) was heated under reflux for 5 hours. After being cooled, the mixture was concentrated under reduced pressure, water (20 mL) was added, the solution basified with aqueous potassium carbonate solution and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using dichloromethane:methanol (1:0 changing to 95:5, by volume) to afford the title compound (75 mg, 65%) as a white solid, mp 192-194° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure, water (20 mL)
  5. additionwas added
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-c219087e12d84648abe57abf03acdd1c
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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