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

HRID 1039811Notes

Reaction equation

HRID 1039811 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aeaebf5e20bb47149506784090804fa5
Source dataset
uspto-grants-2013_10
Patent number
US08551978B2

Reaction notes

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