Dimethylformamide → HCID 86705033、化合物

HRID 1053303ノート

反応式

HRID 1053303 の反応式
[C:1](Cl)(=[O:5])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].[CH2:39]([N:41](CC)CC)C>ClCCl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([N:41]([O:5][CH3:1])[CH3:39])=[O:21])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:34][N:35]([CH3:37])[CH3:36])=[C:24]([CH3:32])[CH:23]=3)[C:15]=2[CH3:33])=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68285893HCID 68285893、化合物

生成物 1

HCID 86705033HCID 86705033、化合物収率 53.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-831fdc1c359245bf88f46caf3ce4ed31
出典データセット
uspto-grants-2016_07
特許番号
US09393247B2

反応ノート

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