Formic Acid → Formamide, N-(4-((3,5-dimethylphenyl)thio)-1,2-dihydro-5-methyl-2-oxo-3-pyridinyl)-

HRID 849987Notes

Reaction equation

HRID 849987 reaction equation
[CH:1](O)=[O:2].[NH2:4][C:5]1[C:6](=[O:21])[NH:7][CH:8]=[C:9]([CH3:20])[C:10]=1[S:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1>C(OCC)=O>[CH:1]([NH:4][C:5]1[C:6](=[O:21])[NH:7][CH:8]=[C:9]([CH3:20])[C:10]=1[S:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)=[O:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 4645802(1H)-Pyridinone, 3-amino-4-((3,5-dimethylphenyl)thio)-5-methyl-

Product 1

HCID 464594Formamide, N-(4-((3,5-dimethylphenyl)thio)-1,2-dihydro-5-methyl-2-oxo-3-pyridinyl)-Yield 58%

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

Formic acid (2 ml) was added to a solution of amine 8a (0.10 g, 0.4 mmole) in ethyl formate (previously distilled over calcium hydride) (8 ml). The mixture was heated under reflux for 12 hours. After evaporation of the volatile substances, the residue was washed twice with ethanol and once with ethyl acetate. It was purified by column chromatography using a mixture of dichloromethane and ethanol (95:5) as eluant and, at the end, ethyl acetate, to give compound 11a (0.06 g, 58%) in the form of a white powder: melting point 221-222° C.; NMR-1H (DMSO-d6) δ 11.96 (1H, s, NH-1), 8.28 (1H, s, NH-3) 7.23 (1H, s, H-6), 6.88 (1H, d, H-4'), 6.78 (2H, s, H-2' and 6'), 2.23 (6H, s, CH3 -3' and 5'), 1.85 (3H, s, CH3 -5). Anal. C15H16N2O2S (C, H, N, S).

Workup

  1. distillationpreviously distilled over calcium hydride) (8 ml)
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 12 hours
  4. customAfter evaporation of the volatile substances
  5. washthe residue was washed twice with ethanol and once with ethyl acetate
  6. customIt was purified by column chromatography
  7. additiona mixture of dichloromethane and ethanol (95:5) as eluant

Sources & evidence

ORD record
ord-83a318a4da004263a0be973561444b69
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

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