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Hexane → 3-(m-Trifluoromethylbenzylmercapto)-2,5-pyridine-dicarboxylic acid dimethyl ester

HRID 2049300
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HRID 2049300 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][SH:7].[H-].[Na+].CCCCCC.[CH3:21][O:22][C:23]([C:25]1[C:30]([N+]([O-])=O)=[CH:29][C:28]([C:34]([O:36][CH3:37])=[O:35])=[CH:27][N:26]=1)=[O:24]>CN(C)C=O.O.C(O)(=O)C>[CH3:21][O:22][C:23]([C:25]1[C:30]([S:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[CH:29][C:28]([C:34]([O:36][CH3:37])=[O:35])=[CH:27][N:26]=1)=[O:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 1412363-(Trifluoromethyl)benzyl mercaptanHCID 539752273-Nitro-2,5-pyridinedicarboxylic acid dimethyl ester

생성물 1

HCID 540247893-(m-Trifluoromethylbenzylmercapto)-2,5-pyridine-dicarboxylic acid dimethyl ester

시약·촉매·용매 3

HCID 176
Acetic Acid
용매
HCID 962Water용매
HCID 6228Dimethylformamide용매2회

실험 절차

The solution of 4.6 g of m-trifluoromethylbenzylmercaptan in 30 ml of dimethylformamide is added to the slurry of 1.08 g of 50% sodium hydride in mineral oil (washed 2 times with hexane), under nitrogen while stirring at room temperature. After several minutes, a clear yellow solution is obtained, which is combined with that of 5.0 g of 3-nitro-2,5-pyridinedicarboxylic acid dimethyl ester in 50 ml of dimethylformamide. The mixture is warmed on the steam bath for 30 minutes at 90° and stirred at room temperature overnight. It is acidified with 2 ml of acetic acid and diluted to 400 ml with a mixture of ice and water. The precipitate formed is collected and recrystallized from methanol-diethyl ether (1:1), to yield the 3-(m-trifluoromethylbenzylmercapto)-2,5-pyridine-dicarboxylic acid dimethyl ester melting at 102°-106°.

후처리

  1. waitAfter several minutes
  2. customa clear yellow solution is obtained
  3. temperatureThe mixture is warmed on the steam bath for 30 minutes at 90°
  4. stirringstirred at room temperature overnight
  5. customThe precipitate formed
  6. customis collected
  7. customrecrystallized from methanol-diethyl ether (1:1)

출처 및 근거

ORD 기록
ord-09b91bbe4fb24612bcaf878f8e04062e
출처 데이터셋
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04197302

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