Triethylamine → 2,6-Dimethyl-3-(2-chloroethyl)-5,6-dihydro-1,4-oxathiin

HRID 620805Notes

Reaction equation

HRID 620805 reaction equation
Cl[CH:2]([CH2:6][CH2:7][Cl:8])[C:3](=[O:5])[CH3:4].[SH:9][CH2:10][CH:11](O)[CH3:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:4][C:3]1[O:5][CH:11]([CH3:12])[CH2:10][S:9][C:2]=1[CH2:6][CH2:7][Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 940323,5-Dichloropentan-2-oneHCID 1025451-Mercapto-2-propanol

Product 1

HCID 145517072,6-Dimethyl-3-(2-chloroethyl)-5,6-dihydro-1,4-oxathiinYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.1 mole (15.4 g.) 3,5-dichloro-2-pentanone, and 0.1 mole (9.2 g.) 1-mercapto-2-propanol was stirred in 100 ml toluene; 0.1 mole (10.4 g.) triethylamine was added dropwise. The mixture was stirred at room temperature overnight, then washed with dilute hydrochloric acid and reluxed with 0.5 g. PTSA, using a Dean-Stark trap to remove water for about 7 hours. The PTSA solution was washed with sodium bicarbonate, dried over magnesium sulfate and the solvent was removed. The product was distilled; bp 80°-82°/0.1 mm. Yield 47%.

Workup

  1. washwashed with dilute hydrochloric acid and reluxed with 0.5 g
  2. customto remove water for about 7 hours
  3. washThe PTSA solution was washed with sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed
  6. distillationThe product was distilled

Sources & evidence

ORD record
ord-a365ace1836d41c4a549625275e951ff
Source dataset
uspto-grants-1989_04
Patent number
US04822813

Reaction notes

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