Triethylamine → HCID 22661044, compound

HRID 392784Notes

Reaction equation

HRID 392784 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)C.Cl.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1.C(N(CC)CC)C>C(O)C>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:6]([C:7]3[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=3)=[N:5][CH:4]=[N:2]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 22661008HCID 22661008, compound

Product 1

HCID 22661044HCID 22661044, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(dimethylamino-methylene)-4-(methyl-sulfonyl)-benzamide (4 g, 15.7 mol), 4-methoxy-phenylhydrazine hydrochloride (2.75 g, 15.7 mmol), triethylamine (2.2 ml, 15.7 mmol) in ethanol (20 ml) was heated to reflux for 25 h. After cooling, the reaction mixture was concentrated to dryness, then diluted with ethyl acetate. The organic phase was washed with water and saturated brine and dried over sodium sulfate. The residue was chromatographed on silica gel using a 70/30 mixture of toluene/dioxane as the eluent, then recrystallized from ethanol to give a light orange solid (0.4 g, 15%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 25 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to dryness
  5. additiondiluted with ethyl acetate
  6. washThe organic phase was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe residue was chromatographed on silica gel using
  9. additiona 70/30 mixture of toluene/dioxane as the eluent
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-552438ef1ef94e139b99c55baae4ec52
Source dataset
uspto-grants-2004_10
Patent number
US06803380B1

Reaction notes

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