Carbon Disulfide → HCID 19979372, compound

HRID 1461767Notes

Reaction equation

C(N(CC)CC)C.[C:8](=[S:10])=S.[CH:11]([C:14]1[C:19]([NH2:20])=[C:18]([CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:15]=1)([CH3:13])[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH:11]([C:14]1[C:19]([N:20]=[C:8]=[S:10])=[C:18]([CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:15]=1)([CH3:12])[CH3:13]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 5.0 g of triethylamine in 10 ml of pyridine is cooled to from -5° C. to -10° C., and 20 ml of carbon disulfide are added dropwise. At -10° C., a solution of 15.0 g of 2,4-diisopropyl-6-(4-chlorophenoxy)-3-aminopyridine in 27 ml of pyridine is slowly added dropwise. The mixture is further stirred at -10° C. for 1 hour. A solution of 10.0 g of N,N'-dicyclohexylcarbodiimide in 10 ml of pyridine is then added. After a further 3 hours at -10° C., the mixture is stirred for 18 hours at room temperature. The reaction mixture is concentrated by evaporation and hexane is added to the residue. Thehhexane solution is filtered off and concentrated by evaporation. 2,4-Diisopropyl-6-(4-chlorophenoxy)-pyrid-3-yl isothiocyanate is obtained in the form of a yellow oil, which is used for the next reaction without being further purified; IR (CCl 4): 2090, 1490, 1220 cm-1.

Workup

additionare added dropwise
waitAfter a further 3 hours at -10° C.
stirringthe mixture is stirred for 18 hours at room temperature
concentrationThe reaction mixture is concentrated by evaporation and hexane
additionis added to the residue
filtrationThehhexane solution is filtered off
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-7a5ca98f2e1141928f89b024ff66ffcb
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05077304

Reaction notes

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