Imidazole → 1-[N-2-chlorophenyl-N-propyl (thiocarbamoyl)]imidazole

HRID 1730027Notes

Reaction equation

HRID 1730027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:12][CH2:13][CH3:14])[C:9](Cl)=[S:10].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:12][CH2:13][CH3:14])[C:9]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[S:10]

Participants

4

Reactant 2

HCID 795Imidazole2×HCID 21319512Carbamothioic chloride, (2-chlorophenyl)propyl-

Product 1

HCID 542482291-[N-2-chlorophenyl-N-propyl (thiocarbamoyl)]imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12.4 g. N-2-chlorophenyl-N-propyl(thiocarbamoyl) chloride and 6.8 g. imidazole were refluxed in 75 ml. dry tetrahydrofuran for 16 hours. A further 2 g. imidazole was then added and the heating continued for 8 hours. After separating the solid formed evaporation of the tetrahydrofuran left an oil which was dissolved in methylene chloride. The resulting organic phase was washed with water, dried with soldium sulphate and the solvent evaporated to leave an oil which crystallised on treatment with light petroleum and chilling to give the product, 1-[N-2-chlorophenyl-N-propyl (thiocarbamoyl)]imidazole, m.p. 59°-61° C.

Workup

  1. customAfter separating the solid
  2. customformed
  3. customevaporation of the tetrahydrofuran
  4. waitleft an oil which
  5. dissolutionwas dissolved in methylene chloride
  6. washThe resulting organic phase was washed with water
  7. dry with materialdried with soldium sulphate
  8. customthe solvent evaporated
  9. customto leave an oil which
  10. customcrystallised on treatment with light petroleum
  11. temperaturechilling

Sources & evidence

ORD record
ord-78dcce6112dc4e2aaeb2b09ec17d2b79
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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