Triethylamine → N-[(1R)-1-(3-Methoxyphenyl)ethyl]-2-nitrobenzenesulfonamide

HRID 732653Notes

Reaction equation

HRID 732653 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18])([O-:10])=[O:9].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C@H:29]([NH2:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1>ClCCl>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C@H:29]([NH:31][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N+:8]([O-:10])=[O:9])(=[O:19])=[O:18])[CH3:30])[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

Product 1

HCID 68910516N-[(1R)-1-(3-Methoxyphenyl)ethyl]-2-nitrobenzenesulfonamideYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.0 ml portion of triethylamine and 1.9 g of orthonitrobenzenesulfonyl chloride were added to a mixed solution of 1.0 g of (1R)-1-(3-methoxyphenyl)ethylamine and 10 ml of dichloromethane under ice-cooling and stirred for 5Hours. Thereafter, work-up and purification were carried out in the standard method to obtain 2.2 g of N-[(1R)-1-(3-methoxyphenyl)ethyl]-2-nitrobenzene sulfonamide as yellow crystals. EN: 335.

Workup

  1. temperaturecooling
  2. customThereafter, work-up and purification

Sources & evidence

ORD record
ord-c84ad1aefed14e22bd83a4af41b2c9cb
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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