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

HRID 849986ノート

反応式

HRID 849986 の反応式
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

参加物

5

反応物 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-

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5dffe156a0c422d8dba0abf79de0d3d
出典データセット
uspto-grants-2000_01
特許番号
US06015820

反応ノート

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