Imidazole → HCID 12783518, compound

HRID 1577819Notes

Reaction equation

HRID 1577819 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:13]=[C:14]([N:18]=[C:19]=[S:20])[CH:15]=[CH:16][CH:17]=1.N1C=CN=C1.[N-]=C=S>C(Cl)(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([NH:18][C:19]([N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[S:3][CH:2]2[CH3:1])=[S:20])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 84462-MethylbenzothiazoleHCID 754493-Chlorophenyl isothiocyanate2×HCID 178418790HCID 178418790, compound

Product 1

HCID 12783518HCID 12783518, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.5 g. of 2-methylbenzothiazoline, 1.7 g. of 3-chlorophenyl isothiocyanate, about 100 ml. of chloroform, and a catalytic amount of imidazole was heated at reflux for several hours. Since thin layer chromatographic analysis showed that reaction was not complete and that some 3-chlorophenyl isothiocyanate had been lost, an additional 1.2 g. of the isothiocyanate was added to the reaction mixture which then was heated at reflux for about 16 hours. The solvent was distilled under reduced pressure and the residue was recrystallized from ethanol to give N-(3-chlorophenyl)-2-methylbenzothiazoline-3-carbothioamide, m.p. 120°-2°. The following elemental microanalysis was obtained:

Workup

  1. additionA mixture of 1.5 g
  2. temperatureat reflux for several hours
  3. customSince thin layer chromatographic analysis showed that reaction
  4. temperaturethen was heated
  5. temperatureat reflux for about 16 hours
  6. distillationThe solvent was distilled under reduced pressure
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-840bf8aecdea402cbd619427f6207bb1
Source dataset
uspto-grants-1981_09
Patent number
US04289766

Reaction notes

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