Aniline → HCID 24762556, compound

HRID 2238291Notes

Reaction equation

HRID 2238291 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P([O-])([O-])(O)=O.[Na+].[Na+].[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].NC1C=CC=CC=1>O.O1CCOCC1>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C:2]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 6115AnilineHCID 124762-Amino-5-chlorobenzoic acidHCID 24203Sodium Phosphate, DibasicHCID 1398824-t-Butylbenzenesulfonyl chloride

Product 1

HCID 24762556HCID 24762556, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Amino-5-chlorobenzoic acid (200 g, 1.17 mol) was added to a solution of sodium hydrogen phosphate (497 g, 3.50 mol) in water (2.4 L) at 70° C. and was stirred until homogeneous (˜10 min). 4-tert-Butylbenzenesulfonyl chloride (353 g 1.52 mol), dissolved in 800 mL p-dioxane, was added to the stirring aniline solution in a steady stream over a ½ hour period via a 1 liter addition funnel. The resultant mixture was stirred at 70° C. overnight. The following day, upon LCMS verification of consumption of the aniline, the reaction mixture was divided into two equal portions for ease of handling. Each portion was poured in a slow stream into two liters of rapidly stirring 2 M HCl/H2O in a four liter Erlenmeyer flask. The resultant precipitate was collected by vacuum filtration and washed well with water. The precipitate from each portion were subsequently combined and dried in vacuo to afford 320 g 2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-benzoic acid as an off-white solid (87% yield): HPLC retention time=2.76 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C., using a 1 mL/min flow rate, a 2.5 minute gradient of 20-100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.08% formic acid/5% water/94.9% acetonitrile)); MS (ES) M+H expected 368.0, found 368.0.

Workup

  1. customThe following day, upon LCMS verification of consumption of the aniline
  2. additionEach portion was poured in a slow stream into two liters
  3. stirringof rapidly stirring 2 M HCl/H2O in a four liter Erlenmeyer flask
  4. filtrationThe resultant precipitate was collected by vacuum filtration
  5. washwashed well with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-be2d0157ad784776b42d429c1925d511
Source dataset
uspto-grants-2010_05
Patent number
US07718683B2

Reaction notes

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