1,3-Dichloroacetone → 2-Acetoxymethyl-4-chloromethyl-4-hydroxythiazoline hydrochloride

HRID 1940883Notes

Reaction equation

HRID 1940883 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH2:8])=[S:7])(=[O:3])[CH3:2].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=[O:12].C(=O)(O)[O-].[Na+]>ClCCCl>[ClH:9].[C:1]([O:4][CH2:5][C:6]1[S:7][CH2:13][C:11]([CH2:10][Cl:9])([OH:12])[N:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 11018908Carbamothioylmethyl acetate

Product 1

HCID 214644562-Acetoxymethyl-4-chloromethyl-4-hydroxythiazoline hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5.33 g of 2-acetoxythioacetamide, prepared according to Example 2, 5.21 g of 1,3-dichloroacetone, 3.44 g of sodium bicarbonate and 20 ml of 1,2-dichloroethane was heated at 40° C. for 15 hours. The mixture was filtered to remove insoluble inorganics and concentrated under reduced pressure to an oil. The oil was taken up in 25 ml of isopropyl alcohol saturated with hydrogen chloride (5N) and 25 ml of isopropanol added to improve stirring. The slurry was stirred for 30 minutes at 0° C. and then filtered. The precipitate was washed with cold IPA and dried at room temperature under reduced pressure. The product 2-acetoxymethyl-4-chloromethyl-4-hydroxythiazoline hydrochloride was obtained in 60% yield (1.66 g).

Workup

  1. customprepared
  2. filtrationThe mixture was filtered
  3. customto remove insoluble inorganics
  4. concentrationconcentrated under reduced pressure to an oil
  5. additionadded
  6. stirringThe slurry was stirred for 30 minutes at 0° C.
  7. filtrationfiltered
  8. washThe precipitate was washed with cold IPA
  9. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-946de4f18da74aaf9ca9ffb2198ed721
Source dataset
uspto-grants-1997_12
Patent number
US05700945

Reaction notes

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