(Chlorothio)formyl chloride → 5-Methoxymethyl-1,3,4-oxathiazol-2-one

HRID 618197Notes

Reaction equation

HRID 618197 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[CH3:6][O:7][CH2:8][C:9]([NH2:11])=[O:10]>C1(C)C=CC=CC=1>[CH3:6][O:7][CH2:8][C:9]1[O:10][C:2](=[O:3])[S:4][N:11]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 1400602-Methoxyacetamide

Product 1

HCID 218503335-Methoxymethyl-1,3,4-oxathiazol-2-oneYield 79.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

Chlorocarbonylsulfenyl chloride (7.35 g) was added to a suspension of methoxyacetamide (5 g) in toluene (30 cm3). The reaction mixture was stirred and heated at 90-100° C. for 5 hours, then cooled. The solvent was removed by evaporation under reduced pressure to give a brown gum (6.6 g). M+ =147; 1H NMR (DMSO-d6): δ3.30(3H,s); 4.30(2H,s) which was used in the next step without further purification.

Workup

  1. temperaturecooled
  2. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-117b7970d9404edba40b1dbf73a5d195
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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