Hydrochloric Acid → Ethyl 2-(Aminosulfonyl)benzoate

HRID 330449Notes

Reaction equation

HRID 330449 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].N[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15].N1C=CC=CC=1.Cl>C(#N)C>[CH2:5]([O:4][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15])=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 728942-Aminobenzenesulfonamide

Product 1

HCID 4652880Ethyl 2-(Aminosulfonyl)benzoateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3.5 g of ethyl chloroformate in 10 ml of anhydrous acetonitrile is dropwise added to a solution of 5.5 g of 2-aminobenzenesulfonamide and 2.5 g of pyridine in 80 ml of anhydrous acetonitrile at room temperature during 2 hours. After stirring at room temperature, the mixture is poured into ice water and acidified with 100 ml of 2N-hydrochloric acid solution. The mixture is extracted with ethyl acetate twice, washed with an aqueous saturated sodium hydrogen carbonate and then with a saturated brine, and dried over anhydrous sodium sulfate. Then the mixture is concentrated under reduced pressure. The residue is crystallized from chloroform to give 6.6 g of the title compound.

Workup

  1. extractionThe mixture is extracted with ethyl acetate twice
  2. washwashed with an aqueous saturated sodium hydrogen carbonate
  3. dry with materialwith a saturated brine, and dried over anhydrous sodium sulfate
  4. concentrationThen the mixture is concentrated under reduced pressure
  5. customThe residue is crystallized from chloroform

Sources & evidence

ORD record
ord-2b5b06707fa64385a4d6f19e266d3619
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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