Dimethylformamide → 3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-5-(4-methoxyphenyl)-N,4-dimethylthiophene-2-carboxamide

HRID 1053259ノート

反応式

HRID 1053259 の反応式
[C:1](Cl)(=[O:5])C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:19][C:18]([C:20](O)=[O:21])=[C:17]([C:23]3[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=3)[C:16]=2[CH3:33])=[CH:11][CH:10]=1.[CH3:34][N:35]([CH:37]=O)[CH3:36].[CH2:39]([N:41](CC)CC)C>ClCCl>[CH3:34][N:35]([CH:37]=[N:30][S:29]([C:26]1[CH:25]=[CH:24][C:23]([C:17]2[C:16]([CH3:33])=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:14][CH:13]=3)[S:19][C:18]=2[C:20]([N:41]([O:5][CH3:1])[CH3:39])=[O:21])=[CH:28][CH:27]=1)(=[O:31])=[O:32])[CH3:36]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 682852325-(4-Methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid2 回

生成物 1

HCID 867050253-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-5-(4-methoxyphenyl)-N,4-dimethylthiophene-2-carboxamide収率 78.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (1.77 g, 1.2 ml, 13.9 mmol) was added drop wise at 0° C. to a solution of 5-(4-methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 7e, 2.8 g, 6.94 mmol) in a mixture of dichloromethane (75 ml) and DMF (1.01 g, 1.1 ml, 13.89 mmol). The so obtained mixture was allowed to come at 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 dissolved in dry dichloromethane (75 ml) and to this was added triethylamine (2.8 g, 3.9 ml, 27.76 mmol) followed by the addition of N, O-dimethylhydroxylamine hydrochloride (1.35 g, 13.89 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then washed with water (2×25 ml) and the organic layer so obtained was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain crude product. The crude product was further purified by column chromatography over silica gel (100-200 mesh) using 80% ethyl acetate in hexane as an eluent to obtain the title compound (2.73 g, 78%).

後処理

  1. customThe so obtained mixture
  2. customto come at room temperature
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customThe residue so obtained
  5. stirringunder stirring
  6. stirringThe reaction mixture was then stirred at room temperature for 2 hr
  7. washThe reaction mixture was then washed with water (2×25 ml)
  8. customthe organic layer so obtained
  9. dry with materialwas dried over anhydrous sodium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customto obtain crude product
  12. customThe crude product was further purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-93c951a48dcb49a5898b1aa3bde16d63
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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