Methyl isothiocyanate → 8-(2,6-Dichlorobenzoylamino)-4-[4-(methyl)thiosemicarbazido]quinoline

HRID 613551Notes

Reaction equation

HRID 613551 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH2:18])=[O:5].[CH3:24][N:25]=[C:26]=[S:27]>C(Cl)CCl>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][C:26]([NH:25][CH3:24])=[S:27])=[O:5]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 19592850HCID 19592850, compound

Product 1

HCID 195929378-(2,6-Dichlorobenzoylamino)-4-[4-(methyl)thiosemicarbazido]quinolineYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 8-(2,6-dichlorobenzoylamino)-4-hydrazinoquinoline (200 mg) and methyl isothiocyanate (54.8 mg) in ethylene chloride (4 ml) was stirred for 2 hours at ambient temperature and then gently refluxed for 24 hours. The mixture was concentrated in vacuo, and the residue was recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-[4-(methyl)thiosemicarbazido]quinoline (213 mg).

Workup

  1. temperaturegently refluxed for 24 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-14cfc9eb5cbd40ebad3461f9301accd1
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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