Tert-Butylamine → 5-[(Tert-butylamino)sulfonyl]-2-chloro-4-fluorobenzoic acid

HRID 1992153Notes

Reaction equation

HRID 1992153 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:15]=[C:14]([F:16])[C:13]([S:17](Cl)(=[O:19])=[O:18])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]>O1CCOCC1>[Cl:6][C:7]1[CH:15]=[C:14]([F:16])[C:13]([S:17]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:19])=[O:18])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 45719302-Chloro-5-chlorosulfonyl-4-fluorobenzoic acid

Product 1

HCID 167781635-[(Tert-butylamino)sulfonyl]-2-chloro-4-fluorobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl amine (77 mL, 0.7 mol, 10 equiv) was added to 300 mL dioxane at 0° C. Ice chips were added to the flask for several minutes before the addition of 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid (20 g, 73.24 mmol, 1 equiv). Both the internal and external temperature of the reaction was maintained at or below 0° C. for 2 h. The reaction was then concentrated half-way and acidified to pH 2 with 1N HCl. The product was extracted into EtOAc. The organics were dried over Na2SO4, filtered and concentrated down to give 2-chloro-5-{[(1,1-dimethylethyl)amino]sulfonyl}-4-fluorobenzoic acid 883-4a as a brown solid (21 g; 92% yield).

Workup

  1. temperatureBoth the internal and external temperature of the reaction was maintained at or below 0° C. for 2 h
  2. concentrationThe reaction was then concentrated half-way
  3. extractionThe product was extracted into EtOAc
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-a5635373b4774415ba4ccfff0fdb6c9a
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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