2-aminosulfonyl-6-isopropyl-N,N-diethylbenzamide → 4-Isopropylsaccharin

HRID 129036Notes

Reaction equation

HRID 129036 reaction equation
N[S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[C:6]=1[C:7]([N:9](CC)CC)=[O:8])(=[O:4])=[O:3]>C(O)(=O)C>[CH:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:5]2[C:6]=1[C:7](=[O:8])[NH:9][S:2]2(=[O:4])=[O:3])([CH3:20])[CH3:19]

Participants

3

Reactant 1

HCID 104024392-aminosulfonyl-6-isopropyl-N,N-diethylbenzamide

Product 1

HCID 117701284-IsopropylsaccharinYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-aminosulfonyl-6-isopropyl-N,N-diethylbenzamide (60 g) in acetic acid (400 mL) was refluxed for 24 hours, then cooled to room temperature. The solvent was removed under vacuum. The oily residue was dissolved in water (500 mL) and the pH was adjusted to 1 with hydrochloric acid (2N). The crude product was collected by filtration, washed with water (300 mL), dried at 60° C. under vacuum for 18 hours and recrystallized from ether-hexane to give 4-isopropylsaccharin (40 g, 90% yield, m.p. 177° C.).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe oily residue was dissolved in water (500 mL)
  3. filtrationThe crude product was collected by filtration
  4. washwashed with water (300 mL)
  5. customdried at 60° C. under vacuum for 18 hours
  6. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-bdc8ff4f39b6452db6ac7a28a047d567
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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