Dimethylformamide → 2-Nitro-4-[(2,2,3,3-tetrafluoropropyl)sulfanyl]aniline

HRID 616144

反応式

HRID 616144 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#N)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN(C)C=O.[BH4-].[Na+].[F:21][C:22]([F:28])([CH:25]([F:27])[F:26])CI>O>[N+:11]([C:3]1[CH:4]=[C:5]([S:8][CH2:9][C:25]([F:27])([F:26])[CH:22]([F:28])[F:21])[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:13])=[O:12]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 5428611,1,2,2-Tetrafluoro-3-iodopropaneHCID 4311764Sodium borohydride

生成物 1

HCID 203711392-Nitro-4-[(2,2,3,3-tetrafluoropropyl)sulfanyl]aniline

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

5 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. of dimethylformamide is treated under nitrogen with 0.97 g. of sodium borohydride in 10 ml. of dimethylformamide at 20°-30° C. After 1 hour at 20°-25° C, 6 g. of 2,2,3,3-tetrafluoro-1-iodopropane is added and the mixture is heated at 100° C for 4 hours. The mixture is cooled, diluted with water and extracted with chloroform. Evaporation of the dried chloroform solution yields 2-nitro-4-(2,2,3,3-tetrafluoropropylthio)aniline as an oil. Acetylation of the latter compound in acetic anhydride with sulfuric acid catalysis according to the first paragraph of Example XXI yields 1-acetamido-2-nitro-4-(2,2,3,3-tetrafluoropropylthio)benzene which can be isolated by extraction into chloroform. Alternatively, this may be prepared by substituting 1-acetamido-2-nitro-4-thiocyanatobenzene in the above alkylation reaction.

後処理

  1. customat 20°-30° C
  2. temperatureThe mixture is cooled
  3. extractionextracted with chloroform
  4. customEvaporation of the dried chloroform solution

出典と根拠

ORDレコード
ord-ca1c6016dd634a4183a0cf3a63eabbb7
出典データセット
uspto-grants-1978_02
特許番号
US04072696

関連ノート

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