Dibenzo-18-crown-6 → N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylfluoroformamidine

HRID 437714Notes

Reaction equation

HRID 437714 reaction equation
[C:1]([C:3]1[C:4]([CH:14]([CH3:16])[CH3:15])=[N:5][S:6][C:7]=1[N:8]=[C:9](Cl)[N:10]([CH3:12])[CH3:11])#[N:2].[F-:17].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C(#N)C>[C:1]([C:3]1[C:4]([CH:14]([CH3:16])[CH3:15])=[N:5][S:6][C:7]=1[N:8]=[C:9]([F:17])[N:10]([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 3

HCID 26541Dibenzo-18-crown-6HCID 522689Potassium FluorideHCID 53844528N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylchloroformamidine

Product 1

HCID 54182572N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylfluoroformamidineYield 20.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 12.8 g of N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylchloroformamidine, 2.9 g of potassium fluoride and a catalytic amount of 2,3,11,12 -dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene, in 60 ml of acetonitrile was stirred at ambient temperature for 12 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was recrystallized from diethyl ether to give 2.5 grams of N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylfluoroformamidine, mp 100°-102°. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-c09a93fb9fbb439a9073a0ec2a1c2105
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

Loading…