Dimethylformamide → HCID 86705033, 화합물

HRID 1518734노트

반응식

HRID 1518734 반응식
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([OH:21])=O)=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[C:24]([CH3:32])[CH:23]=3)[C:15]=2[CH3:33])=[CH:10][CH:9]=1.[CH3:34][N:35]([CH:37]=O)[CH3:36].C(N(CC)CC)C.Cl.[CH3:47][NH:48][O:49][CH3:50]>ClCCl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([N:48]([O:49][CH3:50])[CH3:47])=[O:21])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:37][N:35]([CH3:34])[CH3:36])=[C:24]([CH3:32])[CH:23]=3)[C:15]=2[CH3:33])=[CH:10][CH:9]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68285893HCID 68285893, 화합물

생성물 1

HCID 86705033HCID 86705033, 화합물수율 53.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Oxalyl chloride (0.47 g, 0.32 ml, 3.7 mmol) was added drop wise to a solution of 5-(4-chlorophenyl)-4-methyl-3-(3-methyl-4-sulfamoylphenyl)thiophene-2-carboxylic acid (41d, 0.52 g, 1.23 mmol) in a mixture of dichloromethane (20 ml) and DMF (0.18 g, 0.19 ml, 2.46 mmol) at 0° C. The mixture was then allowed to warm to room temperature and stirred for 1.5 hr under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was then dissolved in dry dichloromethane (20 ml) and cooled to 0° C. To the cooled solution so obtained was then added triethylamine (0.74 g, 1.03 ml, 7.39 mmol), which was then followed by addition of N,O-dimethylhydroxylamine hydrochloride (0.24 g, 2.46 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with DCM (20 ml) and the mixture so obtained was washed with water (2×10 ml). The organic layer obtained was then dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by column chromatography over silica gel (100-200 mesh) using 0.8% methanol in DCM as an eluent to obtain the title compound (0.34 g, 53%).

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturecooled to 0° C
  4. customTo the cooled solution so obtained
  5. stirringunder stirring
  6. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  7. customthe mixture so obtained
  8. washwas washed with water (2×10 ml)
  9. customThe organic layer obtained
  10. dry with materialwas then dried over anhydrous sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was then purified by column chromatography over silica gel (100-200 mesh)

출처 및 근거

ORD 기록
ord-43fec1cc926a42acbf4d34cb846b6752
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09072731B2

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