m-Chloroperbenzoic acid → N-cyano-N'-methyl-methylsulfinylformamidine

HRID 1702475Notes

Reaction equation

HRID 1702475 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH3:8])[S:5][CH3:6])#[N:2].ClC1C=CC=C(C(OO)=[O:17])C=1>CC(C)=O>[C:1]([NH:3][C:4]([S:5]([CH3:6])=[O:17])=[N:7][CH3:8])#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1111031-Cyano-2,3-dimethylisothiourea

Product 1

HCID 12918611N-cyano-N'-methyl-methylsulfinylformamidineYield 62.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred suspension of N-cyano-N',S-dimethylisothiourea (19.4 g) in acetone (700 ml) was added dropwise a solution of m-chloroperbenzoic acid (80% purity, 38.8 g) in acetone (120 ml) at 20°-25° C. After stirring for 1 hr. at the same temperature, the reaction mixture was cooled in an ice bath for 1 hr. and the precipitate was filtered and washed with acetone to give N-cyano-N'-methyl-methylsulfinylformamidine (13.65 g). Yield 62.8%, m.p. 115.5°-116° C.

Workup

  1. temperatureat the same temperature, the reaction mixture was cooled in an ice bath for 1 hr
  2. filtrationand the precipitate was filtered
  3. washwashed with acetone

Sources & evidence

ORD record
ord-532a64afe4c742c1a89c76cd3c3564a8
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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