Hydrochloric Acid → 4-Isopropyl-6-hydroxysaccharin

HRID 266472

Reaction equation

HRID 266472 reaction equation
C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].[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>[CH:8]([C:11]1[CH:21]=[C:20]([OH:22])[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]

Participants

6

Reactant 4

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

Product 1

HCID 100373464-Isopropyl-6-hydroxysaccharinYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

Ethanethiol (43.9 g) was added with stirring to a suspension of aluminum chloride (62.74 g) in chloroform (500 mL) at 0° C. To the resulting solution was added a solution of 4-isopropyl-6-methoxysaccharin (20.0 g) in chloroform (550 mL) during 30 minutes. The resulting solution was warmed to and maintained at 60° C. for 3-4 hours, then poured into ice-water acidified with hydrochloric acid. The resulting solid was collected by filtration, washed with water and dried affording 4-isopropyl-6-hydroxysaccharin, 18.4 g., 97% yield.

Workup

  1. temperatureThe resulting solution was warmed to and
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-306bf5c300b14710a29032a6cc846099
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Linked notes

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