4-Nitrobenzenesulfonyl chloride → N-Ethyl-4-nitro-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-benzenesulfonamide

HRID 1942999Notes

Reaction equation

HRID 1942999 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)[CH3:2].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH2:1]([N:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:19])([C:11]([F:13])([F:14])[F:12])[C:15]([F:16])([F:18])[F:17])=[CH:8][CH:9]=1)[S:29]([C:26]1[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=1)(=[O:30])=[O:31])[CH3:2]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 116663972-(4-(Ethylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86686467N-Ethyl-4-nitro-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-benzenesulfonamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 104 mg 2-(4-Ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 3 ml of pyridine was added 104 mg 4-Nitro-benzenesulfonyl chloride and 10 mg of dimethylaminopyridine. The mixture was stirred for 16 hrs and then concentrated in vacuo. After chromatography (1:3 Ethyl Acetate:Hexane), 129 mg of the named product was obtained. 1H NMR was consistent with the structure.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8a73057208743438a3df24e37bc0475
Source dataset
uspto-grants-2013_03
Patent number
US08389739B1

Reaction notes

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