4-Nitrobenzenesulfonyl chloride → 4-Nitrobenzenesulfonic Acid 2-[3-(Tritylamino)phenyl]ethyl Ester

HRID 1055298노트

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HRID 1055298 반응식
[C:1]([NH:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][OH:29])[CH:24]=[CH:25][CH:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([NH:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][O:29][S:47]([C:44]2[CH:43]=[CH:42][C:41]([N+:38]([O-:40])=[O:39])=[CH:46][CH:45]=2)(=[O:48])=[O:49])[CH:24]=[CH:25][CH:26]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 9237DabcoHCID 516892Sodium BicarbonateHCID 667703302-[3-(Tritylamino)phenyl]ethanol

생성물 1

HCID 866469604-Nitrobenzenesulfonic Acid 2-[3-(Tritylamino)phenyl]ethyl Ester수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of 2-[3-(tritylamino)phenyl]ethanol (5.00 g, 13.2 mmol) and triethylenediamine (2.22 g, 19.8 mmol) in DCM (52.7 mL) under nitrogen at 0° C. was added portion-wise p-nitrobenzenesulfonyl chloride (3.50 g, 15.8 mmol) over a period of 5 min. The resulting mixture stirred at 0° C. for 40 min and then saturated aqueous sodium bicarbonate solution (˜50 mL) was added. The mixture was stirred at room temperature for 10 min and then the layers were separated. The aqueous layer was extracted with DCM (2ט50 mL) and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (7.44 g, 100% yield) as an orange-yellow foamy solid.

후처리

  1. stirringThe mixture was stirred at room temperature for 10 min
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (2ט50 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-131c3292fdf04e7aa0538758f3c25c94
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394275B2

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