Dimethylformamide → 4-(3-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide

HRID 1667701

반응식

HRID 1667701 반응식
[NH2:1][C:2]1[S:3][C:4]([C:14]([NH2:16])=[O:15])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:6]=1.[CH3:17][O:18][CH:19]([O:30][CH3:31])[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22](F)[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C.O>[Cl:13][C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([NH:1][C:22]3[CH:21]=[C:20]([CH:19]([O:30][CH3:31])[O:18][CH3:17])[CH:25]=[CH:24][C:23]=3[N+:26]([O-:28])=[O:27])[S:3][C:4]=2[C:14]([NH2:16])=[O:15])[CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 16658823HCID 16658823, 화합물HCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzene

생성물 1

HCID 866428084-(3-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide수율 47.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3.6 g (15 mmole) of 2-amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.2), 3.9 g (17.9 mmole) of 4-(dimethoxymethyl)-2-fluoro-1-nitro-benzene (IV.2a), 7.3 g (22.5 mmole) cesium carbonate, and 30 mL of dimethylformamide was heated at 70 degrees for 18 hours. The mixture was cooled, diluted with 150 mL of ethyl acetate and 100 mL of water. The ethyl acetate layer was washed once with 100 mL of brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (50:50) to give 3.2 g of 4-(3-chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.2a).

후처리

  1. temperaturewas heated at 70 degrees for 18 hours
  2. temperatureThe mixture was cooled
  3. washThe ethyl acetate layer was washed once with 100 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexanes-ethyl acetate (50:50)

출처 및 근거

ORD 기록
ord-84d4393fea4048b4a29b84a4af0a00fe
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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