Water → HCID 15070293, compound

HRID 1073031Notes

Reaction equation

HRID 1073031 reaction equation
[SH:1][CH:2]([CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[OH-].[K+].O.Cl[C:15]1[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][CH3:24])[N:16]=1>CC(C)=O>[CH3:24][O:23][C:17]1[N:18]=[C:19]([O:21][CH3:22])[N:20]=[C:15]([S:1][CH:2]([CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:5])=[O:4])[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 15070292HCID 15070292, compound

Product 1

HCID 15070293HCID 15070293, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture solution of 6.0 g of 2-mercapto-2-cyclopentyl acetic acid, 4.2 g of potassium hydroxide and 50 ml of water, a solution of 30 ml of acetone and 6.6 g of 2-chloro-4,6-dimethoxy S-triazine was added at a temperature of from 0° to 5° C. for 20 mimutes. Then, the reaction mixture was stirred at room temperature for 1.5 hours. Acetone was removed by distillation under reduced pressure, and the residue was extracted with ethyl ether. The ethyl ether layer was removed, and the aqueous layer was adjsuted to pH 2 to 3 with a 5% hydrochloric acid aqueous solution and extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried. Then, ethyl acetate was removed by distillation under reduced pressure to obtain a white solid. The solid was recrystallized from isopropyl ether and n-hexane to obtain 4.5 g of the desired product.

Workup

  1. customAcetone was removed by distillation under reduced pressure
  2. extractionthe residue was extracted with ethyl ether
  3. customThe ethyl ether layer was removed
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customThen, ethyl acetate was removed by distillation under reduced pressure
  9. customto obtain a white solid
  10. customThe solid was recrystallized from isopropyl ether and n-hexane

Sources & evidence

ORD record
ord-de5a35619b344678a3c270b166782457
Source dataset
uspto-grants-1990_11
Patent number
US04968340

Reaction notes

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