Sodium Thiosulfate → HCID 13394557, compound

HRID 276711Notes

Reaction equation

HRID 276711 reaction equation
[Cl:1][CH2:2][CH2:3]SC1C=CC(C(O)=O)=CC=1.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]O)=[O:22])[CH:16]=1.[S:25]([O-:29])([O-])(=[O:27])=S.[Na+].[Na+]>C(Cl)Cl.O>[Cl:1][CH2:2][CH2:3][S:25]([C:20]1[CH:19]=[CH:18][C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1)(=[O:29])=[O:27]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 183166944-(2-Chloroethylthio)benzoic acid

Product 1

HCID 13394557HCID 13394557, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

4-(2-Chloroethylsulfanyl)-benzoic acid (18.4 mmol) is suspended in methylene chloride (60 ml) and cooled to −10C. m-Chloroperbenzoic acid (38.6 mmol) are added dropwise in methylene chloride (60 ml) and the mixture is stirred for e hours at −10° C. The mixture is diluted methylene chloride (100 ml) and a 5% solution of sodium thiosulfate in water is added and the mixture vigorously stirred. The mixture is extracted, washed with water and and dried over sodium sulfate and evaporated. The crude product is recrystallized from ethylacetate and the solid filtered of and dried (vacuum). 2.19 g of a pale powder with mp. 142-144° C., Rf=0.37 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. temperaturecooled to −10C
  2. stirringthe mixture vigorously stirred
  3. extractionThe mixture is extracted
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe crude product is recrystallized from ethylacetate
  8. filtrationthe solid filtered of and
  9. customdried (vacuum)

Sources & evidence

ORD record
ord-e28ffb9f082942739d856da13297091f
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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