Sodium Carbonate → 2(1H)-Pyridinone, 3-amino-4-((3,5-dimethylphenyl)thio)-5-ethyl-

HRID 849986Notes

Reaction equation

HRID 849986 reaction equation
NC1C(=O)NC=C(C)C=1SC1C=C(C)C=C(C)C=1.[CH2:19]([C:21]1[C:22]([S:31][C:32]2[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=2)=[C:23]([N+:28]([O-])=O)[C:24](=[O:27])[NH:25][CH:26]=1)[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH2:28][C:23]1[C:24](=[O:27])[NH:25][CH:26]=[C:21]([CH2:19][CH3:20])[C:22]=1[S:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4645752(1H)-Pyridinone, 4-((3,5-dimethylphenyl)thio)-5-ethyl-3-nitro-HCID 4645802(1H)-Pyridinone, 3-amino-4-((3,5-dimethylphenyl)thio)-5-methyl-

Product 1

HCID 4645812(1H)-Pyridinone, 3-amino-4-((3,5-dimethylphenyl)thio)-5-ethyl-Yield 64.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

As described for compound 8a in example 17, stannous chloride dihydrate (6.67 g, 29.6 mmoles) was added to a suspension of compound 7b (1.80 g, 5.9 mmoles) in ethyl acetate (100 ml). The mixture was heated at 70° C. under an argon atmosphere for 1 hour. After cooling to 0° C., the solution was neutralised with a saturated solution of sodium carbonate (90 ml). The precipitate was removed by filtration. The filtered phases were separated and the aqueous phase was extracted with dichloromethane. The collected organic phases were washed with a saturated aqueous sodium chloride solution (3×120 ml), dried over magnesium sulphate and evaporated. The residue was purified by column chromatography with a mixture of dichloromethane and ethanol (9:1) as eluant to give the product 8b (1.04 g, 64%) in the form of a pale beige solid: melting point 208-209° C.; NMR-1H (DMSO-d6) δ 11.51 (1H, s, NH-1), 6.81 (1H, s, H-4'), 6.68 (2H, s, H-2' and 6'), 6.56 (1H, s, H-6), 5.43 (2H, s, NH2 -3), 2.40 (2H, q, J=7.5 Hz, CH2CH3), 2.21 (6H, s, CH3 -3' and 5'), 1.04 (3H, t, J=7 Hz, CH2CH3). Anal. C15H18N2OS 0.25H2O (C, H, N, S).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customThe precipitate was removed by filtration
  3. customThe filtered phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. washThe collected organic phases were washed with a saturated aqueous sodium chloride solution (3×120 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by column chromatography with a mixture of dichloromethane and ethanol (9:1) as eluant

Sources & evidence

ORD record
ord-b5dffe156a0c422d8dba0abf79de0d3d
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

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