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

HRID 1518990Notes

Reaction equation

HRID 1518990 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-40ae53a1b80a44a7baa4fc46a4936895
Source dataset
uspto-grants-2015_07
Patent number
US09073834B2

Reaction notes

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