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

HRID 616144노트

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HRID 616144 반응식
[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]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 5428611,1,2,2-Tetrafluoro-3-iodopropaneHCID 4311764Sodium borohydride

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ca1c6016dd634a4183a0cf3a63eabbb7
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04072696

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