Ethylene Glycol → Acetamide, N-(6-amino-5-formyl-2,4-dimethyl-3-pyridinyl)-

HRID 1730645Notes

Reaction equation

HRID 1730645 reaction equation
C(O)CO.[NH2:5][C:6]1[N:24]=[C:23]([CH3:25])[C:22]([NH:26][C:27](=[O:29])[CH3:28])=[C:21]([CH3:30])[C:7]=1[C:8](NNS(C1C=CC=CC=1)(=O)=O)=[O:9].C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)Cl>[NH2:5][C:6]1[N:24]=[C:23]([CH3:25])[C:22]([NH:26][C:27](=[O:29])[CH3:28])=[C:21]([CH3:30])[C:7]=1[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 10340Sodium CarbonateHCID 12297945HCID 12297945, compound

Product 1

HCID 12297946Acetamide, N-(6-amino-5-formyl-2,4-dimethyl-3-pyridinyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

Ethylene glycol (80 ml.) is heated in an oil-bath at 170° C. until the internal temperature reaches 160° C. N1 -(2-amino-5-acetamido-4,6-dimethylnicotinoyl)-N2 -benzenesulfonyl hydrazine (8.0 g., 21.2 mmole) is added and the mixture stirred until the internal temperature returns to 160° C. Anhydrous sodium carbonate (5.6 g.) is added in one portion, heating is continued for 30 seconds and the reaction mixture cooled rapidly and poured into water (320 ml.). The product is isolated by continuous extraction with methylene chloride for about 24 hours to give 2.90 g. (66%) of crude product. Following purification by crystallization from ethanol the pure product melts at 270°-275° C. (dec.) with rapid heating.

Workup

  1. customreaches 160° C
  2. temperatureheating
  3. temperaturethe reaction mixture cooled rapidly
  4. customto give 2.90 g
  5. custompurification
  6. customby crystallization from ethanol the pure product melts at 270°-275° C. (dec.) with rapid heating

Sources & evidence

ORD record
ord-410dff877ec44d2d80c2875c688a5daf
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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