tert-Butyl-3-aminobenzoate → 3-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester

HRID 62816

Reaction equation

HRID 62816 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:16]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][S:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:22])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2737408tert-Butyl-3-aminobenzoateHCID 3164136Pyridine-3-sulfonyl chloride

Product 1

HCID 673108723-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl esterYield 104.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl-3-aminobenzoate (100 mg, 0.5 mmol) and pyridine-3-sulfonylchloride (110 mg, 0.5 mmol) in pyridine (5 ml) was heated to 50° C. for 90 min. On cooling, the reaction was diluted with toluene (100 ml) and concentrated in vacuo. This was repeated with further aliquots of toluene until all the pyridine had been removed to afford the title compound as a yellow oil (175 mg). HPLC retention time 4.27 min. Mass spectrum (ES+) m/z 335 (M+H).

Workup

  1. temperatureOn cooling
  2. concentrationconcentrated in vacuo
  3. customhad been removed

Sources & evidence

ORD record
ord-7d115dd033a8422f9a090d4e1b705403
Source dataset
uspto-grants-2016_09
Patent number
US09447033B2

Linked notes

Loading…