Methyl fluorosulfate → Azolimine

HRID 442030Notes

Reaction equation

HRID 442030 reaction equation
[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[N:9]=[C:8]2[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14]OS(F)(=O)=O.[OH-].[Na+]>C(Cl)Cl>[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[N:9]([CH3:14])[C:8]2=[NH:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9870Methyl fluorosulfateHCID 14798Sodium HydroxideHCID 20311581HCID 20311581, compound

Product 1

HCID 38684Azolimine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.2 g. of 1-phenyl-2-amino-4-oxo-2-imidazoline, 15 ml. methylene chloride and 3.6 ml. of methylfluorosulfonate was left to stir at room temperature for 20 hours. The reaction was stopped and filtered to give 1.9 g. (94%) of the acid salt of the product. The isolation of the free base (m.p. 164°) is made by treating the salt with aqueous sodium hydroxide.

Workup

  1. additionA mixture of 1.2 g
  2. filtrationfiltered
  3. customto give 1.9 g

Sources & evidence

ORD record
ord-3506bb9a5cad41c68db1c90596acea6f
Source dataset
uspto-grants-1977_08
Patent number
US04044021

Reaction notes

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