3-Nitrobenzenesulfonyl chloride → Ethyl 3-benzenesulphonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

HRID 1596561Notes

Reaction equation

HRID 1596561 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:19][CH:20]=1>N1C=CC=CC=1>[C:32]1([S:29]([NH:28][CH:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][S:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)(=[O:12])=[O:11])[CH:16]=2)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:30])=[O:31])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 15907252Ethyl 3-(3-aminophenyl)-3-benzenesulphonylamino-propionate

Product 1

HCID 11421258Ethyl 3-benzenesulphonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionateYield 84.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

382 mg of 3-nitrobenzenesulphonyl chloride were added at 0° C. to a solution of 500 mg of (1d) in 4 ml of pyridine. After a reaction time of 1 h at 0° C. and 2 h at room temperature, the mixture was concentrated, treated with 1 N HCl and extracted with dichloromethane. After drying over MgSO4, the solvent was removed and 649 mg of a solid were obtained.

Workup

  1. concentrationAfter a reaction time of 1 h at 0° C. and 2 h at room temperature, the mixture was concentrated
  2. additiontreated with 1 N HCl
  3. extractionextracted with dichloromethane
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-644dc95f66c443b1b60b9e8097f963d0
Source dataset
uspto-grants-2001_09
Patent number
US06291503B1

Reaction notes

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