Phosgeniminium chloride → N'-(4-cyano-3-propyl-5-isothiazolyl)-N,N-dimethylchloroformamidine

HRID 437716Notes

Reaction equation

HRID 437716 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH2:7][CH2:8][CH3:9])[C:3]=1[C:10]#[N:11].[Cl-].[Cl:13][C:14](Cl)=[N+:15]([CH3:17])[CH3:16]>ClCCl>[C:10]([C:3]1[C:4]([CH2:7][CH2:8][CH3:9])=[N:5][S:6][C:2]=1[N:1]=[C:14]([Cl:13])[N:15]([CH3:17])[CH3:16])#[N:11]

Participants

4

Reactant 2

HCID 2723945Phosgeniminium chlorideHCID 214267405-Amino-3-propyl-4-isothiazolecarbonitrile

Product 1

HCID 53949652N'-(4-cyano-3-propyl-5-isothiazolyl)-N,N-dimethylchloroformamidineYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the manner of Example VI, a solution of 8.4 g of 5-amino-4-cyano-3-propylisothiazole in 50 ml of dichloromethane was treated with 9.8 g of N-(dichloromethylene)-N,N-dimethylammonium chloride. After removal of the volatile materials under reduced pressure, the residue was recrystallized from 90:10 hexane:benzene to yield 6.5 g of N'-(4-cyano-3-propyl-5-isothiazolyl)-N,N-dimethylchloroformamidine, mp 108°-109°. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customAfter removal of the volatile materials under reduced pressure
  2. customthe residue was recrystallized from 90:10 hexane

Sources & evidence

ORD record
ord-d51fd68ff1724b3d9e11f4d4653d0b6d
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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