Dibenzo-18-crown-6 → N'-acetyl-N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylurea
Reaction equation
[C:1]([O-:4])(=O)[CH3:2].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)[O:8]C1.[C:32]([C:34]1[C:35]([CH:45]([CH3:47])[CH3:46])=[N:36][S:37][C:38]=1[N:39]=[C:40](Cl)[N:41]([CH3:43])[CH3:42])#[N:33]>C(#N)C>[C:1]([N:39]([C:38]1[S:37][N:36]=[C:35]([CH:45]([CH3:47])[CH3:46])[C:34]=1[C:32]#[N:33])[C:40](=[O:8])[N:41]([CH3:43])[CH3:42])(=[O:4])[CH3:2]Participants
Procedure
A mixture of 4.9 g of potassium acetate, 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 vigorously during 45 minutes. Then 12.8 grams of N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylchloroformamidine in acetonitrile were added. The reaction mixture stood at ambient temperature for 16 hours. Thin layer chromatographic analysis indicated that the reaction had not gone to completion. The reaction mixture was stirred at ambient temperature for 3 days, at which time thin layer chromatographic analysis indicated the reaction to be complete. The reaction mixture was filtered and the filtrate evaporated, under reduced pressure. The residue was slurried in diethyl ether to give a solid. The solid was collected by filtration, then slurried in water to give 10.8 g of N'-acetyl-N'-(4-cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylurea; mp 128°-130°. The nmr and the ir spectra were consistent with the assigned structure. The uv spectrum confirmed the structure.
Workup
- customthe reaction
- filtrationThe reaction mixture was filtered
- customthe filtrate evaporated, under reduced pressure
- customto give a solid
- filtrationThe solid was collected by filtration
Sources & evidence
- ORD record
- ord-59d5579531674959acbb64fc65e91049
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04032321
Reaction notes
Loading…