Triethylamine → Propanamide, N-(4-((3,5-dimethylphenyl)thio)-1,2-dihydro-5-methyl-2-oxo-3-pyridinyl)-

HRID 849988Notes

Reaction equation

HRID 849988 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl-].[Cl-].[Ca+2].[NH2:9][C:10]1[C:11](=[O:26])[NH:12][CH:13]=[C:14]([CH3:25])[C:15]=1[S:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1.C(N(CC)CC)C>ClCCl>[CH3:25][C:14]1[C:15]([S:16][C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)=[C:10]([NH:9][C:1](=[O:4])[CH2:2][CH3:3])[C:11](=[O:26])[NH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 4645802(1H)-Pyridinone, 3-amino-4-((3,5-dimethylphenyl)thio)-5-methyl-HCID 5284359Calcium Chloride

Product 1

HCID 464596Propanamide, N-(4-((3,5-dimethylphenyl)thio)-1,2-dihydro-5-methyl-2-oxo-3-pyridinyl)-Yield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Freshly distilled propionyl chloride (0.04 ml, 0.41 mmole) (the receptacle is fitted with a trap containing CaCl2) was added to a solution of amine 8a (0.10 g, 0.40 mmole) and triethylamine (0.04 ml, 0.38 mmole) in dichloromethane (5 ml) at 0° C. The mixture was agitated at ambient temperature for 5 hours. The solvent was evaporated, water was added and the solid was isolated by filtration. The residue was purified by column chromatography using a mixture of dichloromethane and ethanol (94:6) as eluant and at the end ethyl acetate in order to obtain the compound 11c (0.10 g, 90%) in the form of a white powder: melting point 186-188° C.; NMR-1H (DMSO-d6) δ 11.86 (1H, s, NH-1), 8.60 (1H, s, NH-3), 7.21 (1H, s, H-6), 6.88 (1H, s, H-4'), 6.80 (2H, s, H-2' and 6'), 4.04 (2H, q, J=7 Hz, COCH2CH3), 2.22 (6H, s, CH3 -3' and 5'), 1.82 (3H, s, CH3 -5), 1.20 (3H, t, J=7 Hz, COCH2CH3). Anal. C17H20N2O2S . 1.25H2O (C, H, N, S).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. customthe solid was isolated by filtration
  4. customThe residue was purified by column chromatography
  5. additiona mixture of dichloromethane and ethanol (94:6) as eluant

Sources & evidence

ORD record
ord-26deb899382e4a95a1c426a24b756b9e
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

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