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

HRID 849986노트

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HRID 849986 반응식
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

참가 물질

5

반응물 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-

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5dffe156a0c422d8dba0abf79de0d3d
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015820

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