(Chlorothio)formyl chloride → 5-[2-(4-Hydroxy-3,5-di-tert-butylphenyl)ethyl]-1,3,4-oxathiazol-2-one

HRID 4177

Reaction equation

HRID 4177 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:12][CH2:13][C:14]([NH2:16])=[O:15])=[CH:4][C:3]=1[C:17]([CH3:20])([CH3:19])[CH3:18].Cl[C:22]([S:24]Cl)=[O:23]>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][C:5]([CH2:12][CH2:13][C:14]2[O:15][C:22](=[O:23])[S:24][N:16]=2)=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 122714763-(3,5-Di-tert-butyl-4-hydroxyphenyl)propanamide

Product 1

HCID 201529325-[2-(4-Hydroxy-3,5-di-tert-butylphenyl)ethyl]-1,3,4-oxathiazol-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 13.45 grams of 3-[4-hydroxy-3,5-di- tert-butylphenyl]propionamide in 150 ml of toluene is admixed with 20.22 grams of chlorocarbonyl sulfenyl chloride added dropwise. After heating the reaction mixture at 60° C. for 20 hours, the solvent is removed under reduced pressure. The residue is recrystallized from heptane to give the title compound as a pale yellow crystalline solid: mp 82°-86° C.

Workup

  1. additionadded dropwise
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-aceb139e08c74474b4660ef26669537f
Source dataset
uspto-grants-1988_02
Patent number
US04724246

Linked notes

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