1,3-Dichloroacetone → 4-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-

HRID 1741785Notes

Reaction equation

HRID 1741785 reaction equation
Cl.[CH3:2][N:3]([CH2:5][C:6]([NH2:8])=[S:7])[CH3:4].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=[O:12].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:12][C:11]1([CH2:10][Cl:9])[CH2:13][S:7][C:6]([CH2:5][N:3]([CH3:4])[CH3:2])=[N:8]1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 13121932N,N-Dimethylaminothioacetamide hydrochloride

Product 1

HCID 103307024-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-Yield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of dimethylaminothioacetamide hydrochloride 54.0 g, 350 mmol), 1,3-dichloroacetone (52.0 g, 409 mmol) and sodium bicarbonate (64.0 g, 762 mmol) in 300 ml of toluene was stirred at 60° C. for 2 hours. The hot reaction solution was then cooled and salts which had precipitated during the reaction were removed by filtration. An equal volume of petroleum ether was then added to the filtrate and solids precipitated. These solids were recovered by filtration to afford 55.5 g of titled compound.

Workup

  1. temperatureThe hot reaction solution was then cooled
  2. customsalts which had precipitated during the reaction
  3. customwere removed by filtration
  4. additionAn equal volume of petroleum ether was then added to the filtrate and solids
  5. customprecipitated
  6. filtrationThese solids were recovered by filtration

Sources & evidence

ORD record
ord-8259b7f042744b138ef54356a6352e76
Source dataset
uspto-grants-1994_08
Patent number
US05334725

Reaction notes

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