Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 13768090, compound

HRID 1789364Notes

Reaction equation

HRID 1789364 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[S:4].[Cl:17][CH2:18][CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:19][CH2:18][Cl:17])=[CH:12][CH:11]=1)=[S:4]

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 13768084HCID 13768084, compound

Product 1

HCID 13768090HCID 13768090, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g of N-methyl-2-(4-hydroxyphenyl)thiazolidine-3-carbothioamide, 4.6 g of 1-chloro-2-tosyloxyethane, 4 g of potassium carbonate and 20 ml of dimethylformamide is stirred at room temperature for 2 days and further stirred at 50° C. for 20 hours. The mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with an aqueous 10% sodium hydroxide solution and water, and dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=2:8), and the resultant product is recrystallized from ethanol. 3.07 g of N-methyl-2-[4-(2-chloroethyloxy)phenyl]thiazolidine-3-carbothioamide are obtained. Yield: 51.9%.

Workup

  1. stirringfurther stirred at 50° C. for 20 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. additionWater is added to the residue
  5. extractionthe aqueous mixture is extracted with ethyl acetate
  6. washThe extract is washed with an aqueous 10% sodium hydroxide solution and water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=2:8)
  11. customthe resultant product is recrystallized from ethanol

Sources & evidence

ORD record
ord-a487da4d0ad342668dd109913a8681fe
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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