Acetic Acid → N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline

HRID 2258617노트

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HRID 2258617 반응식
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])(=[O:14])=[O:13])=[CH:8][CH:7]=1.C(O)(=O)C.N([O-])=O.[Na+]>O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[C:20]([F:22])[C:19]([N+:1]([O-:4])=[O:2])=[CH:18][C:17]=2[F:23])(=[O:14])=[O:13])=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 8500594N-(2,5-difluorophenyl)-4-methylbenzenesulfonamideHCID 23668193Sodium Nitrite

생성물 1

HCID 22921537N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline수율 98.9%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
90 °C

실험 절차

A stirred solution of 20 mL (0.427 mole) of 90% nitric acid (fuming) in 170 mL of water was cooled in an ice-water bath, and 22.0 grams (0.077 mole) of N-(4-methylphenylsulfonyl)-2,5-difluoroaniline was added. To this mixture was added 170 mL of acetic acid and then 0.5 gram (0.008 mole) of sodium nitrite. Upon completion of the addition, the reaction mixture was warmed to 90° C., where it stirred for about 2.5 hours. The reaction mixture was then cooled and poured into cold water. The resultant precipitate was collected by filtration and dried, yielding about 25 grams of N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of the addition
  2. temperatureThe reaction mixture was then cooled
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried

출처 및 근거

ORD 기록
ord-53879eab8ecb4ad29f6f0088f467a3ce
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05661108

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