Hydrochloric Acid → 4-Isopropyl-6-hydroxysaccharin

HRID 864737Notes

Reaction equation

HRID 864737 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.[CH:8]([C:11]1[CH:21]=[C:20]([O:22]C)[CH:19]=[C:18]2[C:12]=1[C:13](=[O:24])[NH:14][S:15]2(=[O:17])=[O:16])([CH3:10])[CH3:9].Cl>C(Cl)(Cl)Cl>[OH:22][C:20]1[CH:19]=[C:18]2[C:12]([C:13](=[O:24])[NH:14][S:15]2(=[O:17])=[O:16])=[C:11]([CH:8]([CH3:10])[CH3:9])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 101473624-Isopropyl-6-methoxysaccharin

Product 1

HCID 100373464-Isopropyl-6-hydroxysaccharinYield 97.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

An alternative procedure was also used. To a stirred suspension of 62.74 g (0.47 mol) of AlCl3 in 500 mL of chloroform at 0° was added 43.9 g (0.7 mol) of ethanethiol. Within minutes a clear solution formed. To this a solution of 20.0 g (0.078 mol) of 4-isopropyl-6-methoxysaccharin in 550 mL of chloroform was added over a 30-min period. This solution was allowed to warm to RT and stirred for 3-4 hr at 60°. After cooling, the mixture was poured into ice-water and acidified with dilute HCl. The solid which separated was collected by filtration, washed with water and dried to give 18.4 g (97%) of 6-hydroxy-4-isopropylsaccharin.

Workup

  1. customWithin minutes a clear solution formed
  2. temperatureAfter cooling
  3. customThe solid which separated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-839778f669534e359013e1a6fd3a87de
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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