Hydrochloric Acid → Pentyl 4-sulfamoylbenzoate

HRID 981066Notes

Reaction equation

HRID 981066 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl>C(O)CCCC>[CH2:6]([O:2][C:1](=[O:3])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:5][CH2:4][CH2:9][CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 8739Carzenide

Product 1

HCID 23274926Pentyl 4-sulfamoylbenzoate

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A slurry of 32.1 g (0.15 mole) of p-carboxybenzenesulfonamide, methyl ester in 400 ml of n-pentanol was treated with 25 g of anhydrous hydrogen chloride and the mixture was heated at reflux temperature for 4 hr. The reaction was again treated by the slow addition of anhydrous hydrogen chloride during 8 hr of slow distillation. Approximately 150 ml of distillate was collected. The distillate was replaced in the reaction mixture with 150 ml of n-pentanol and the solution was heated at reflux for 66 hr. Excess pentanol and hydrogen chloride were removed by distillation under vacuum. The residue wad crystallized from a mixture of 350 ml of ethyl acetate and 500 ml of petroleum ether to give 22.0 g (54%) of white flakes, mp 96°-98° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 4 hr
  3. distillationApproximately 150 ml of distillate was collected
  4. temperaturethe solution was heated
  5. temperatureat reflux for 66 hr
  6. customExcess pentanol and hydrogen chloride were removed by distillation under vacuum
  7. customThe residue wad crystallized from a mixture of 350 ml of ethyl acetate and 500 ml of petroleum ether
  8. customto give 22.0 g (54%) of white flakes, mp 96°-98° C.

Sources & evidence

ORD record
ord-5c1d7f9c0f764f058afcbc09456636fe
Source dataset
uspto-grants-1991_02
Patent number
US04990523

Reaction notes

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