4-Chlorobenzenesulfonamide → 1,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoate

HRID 1638552

Reaction equation

HRID 1638552 reaction equation
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:11]([C:10]2[CH:9]=[CH:8][C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[CH:15][CH:14]=2)=[O:13])(=[O:25])=[O:26])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 668244-ChlorobenzenesulfonamideHCID 27609544-(tert-Butoxycarbonyl)benzoic acid

Product 1

HCID 545475071,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoateYield 122%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet. Methylene chloride (2 liters) was placed in the reaction flask and terephthalic acid mono-t-butyl ester (127.5 g), 4-dimethylaminopyridine (70.06 g), and 4-chlorobenzenesulfonamide (110.04 g) were added sequentially using methylene chloride (400 ml) to wash down the solids. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added in portions over 10 min using methylene chloride (100 ml) to wash down the solid. After the reaction mixture was stirred overnight at room temperature, it was evaporated to dryness. The residue was partitioned between ethyl acetate and water. The organic solution was washed with 20% (w/v) aqueous citric acid, saturated aqueous NaHCO3 and brine; dried (Na2SO4); and evaporated to a white solid. After drying in a vacuum oven at 50°, the ester (277 g, 100%) was obtained in a sufficiently pure state to be used directly for the next step; TLC, Rf =0.43, methanol:chloroform (15:85). (Further purification was possible by recrystallization from ethanol/water; mp above 300°).

Workup

  1. customA 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet
  2. washto wash down the solids
  3. addition1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added in portions over 10 min
  4. washto wash down the solid
  5. customit was evaporated to dryness
  6. customThe residue was partitioned between ethyl acetate and water
  7. washThe organic solution was washed with 20% (w/v) aqueous citric acid, saturated aqueous NaHCO3 and brine
  8. dry with materialdried (Na2SO4)
  9. customand evaporated to a white solid
  10. customAfter drying in a vacuum oven at 50°

Sources & evidence

ORD record
ord-5ada9057b0c34269a5af2e90a0b9ce6e
Source dataset
uspto-grants-1989_11
Patent number
US04880780

Linked notes

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