Isopropanol → HCID 178470768, compound

HRID 634958Notes

Reaction equation

HRID 634958 reaction equation
[C:1](=[S:4])([S-:3])[NH2:2].[NH4+].C(O)(C)C.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>O>[CH2:17]([O:16][C:14]([CH2:13][C:12]1[N:2]=[C:1]([SH:3])[S:4][CH:11]=1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 69484Ethyl 4-chloroacetoacetateHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178470768HCID 178470768, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 180.0 g (1.63 mols) of ammonium dithiocarbamate was added 1.5 liters of isopropyl alcohol, the mixture was stirred and then 268.9 g (1.63 mols) of ethyl 4-chloro-3-oxobutanoate was added dropwise to the mixture. After stirring the resultant mixture for 3 hours under refluxing, 300 ml of water was added to the reaction mixture, the mixture was cooled to room temperature and crystals formed were collected by filtration under a reduced pressure to obtain crude crystals. The crude crystals were recrystallized from ethyl acetate to obtain 188 g (yield 57%) of 4-ethoxycarbonylmethyl-2-mercaptothiazole.

Workup

  1. temperatureunder refluxing
  2. customcrystals formed
  3. filtrationwere collected by filtration under a reduced pressure
  4. customto obtain crude crystals
  5. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-22ec9ce4adfa4f94b6cc27b7408e9e2b
Source dataset
uspto-grants-2001_02
Patent number
US06184386B2

Reaction notes

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