Methyl fluorosulfate → HCID 20311569, compound

HRID 2420364Notes

Reaction equation

HRID 2420364 reaction equation
[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[N:9]([CH3:13])[C:8]2=[NH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15]OS(F)(=O)=O>C(Cl)Cl>[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[N:9]([CH3:13])[C:8]2=[N:14][CH3:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 386842-Imino-3-methyl-1-phenyl-4-imidazolidinone

Product 1

HCID 20311569HCID 20311569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.78 g. of 1-phenyl-2-imino-3-methyl-4-oxoimidazolidine, 40 ml. dry methylene chloride and 6 ml. of methylfluorosulfonate were mixed and stirred in a flash equipped with a drying tube at room temperature. After 20 hours the solid was filtered and the filtrate was stripped to dryness. The residue was treated with 30 ml. of water and extracted once with ether. The aqueous layer was separated and added slowly to 12 ml. of 5N NaOH with cooling and stirring. The white precipitate was filtered, washed with water and dried. Thin-layer chromatography showed a single spot (Rf 0.6, 5% EtOH·CH2Cl2). The yield was 2.75 g. (68%), m.p. 116°-118° C.

Workup

  1. customequipped with a drying tube at room temperature
  2. filtrationAfter 20 hours the solid was filtered
  3. additionThe residue was treated with 30 ml
  4. extractionof water and extracted once with ether
  5. customThe aqueous layer was separated
  6. additionadded slowly to 12 ml
  7. temperatureof 5N NaOH with cooling
  8. stirringstirring
  9. filtrationThe white precipitate was filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-b42b1f827a7a43859728f7e9b831ec31
Source dataset
uspto-grants-1978_08
Patent number
US04110445

Reaction notes

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