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

HRID 2210235Notes

Reaction equation

HRID 2210235 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-321988e072ab4405b68f9c822890e557
Source dataset
uspto-grants-1995_10
Patent number
US05457206

Reaction notes

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