Methyl iodide → HCID 54307693, compound

HRID 1076190Notes

Reaction equation

HRID 1076190 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[S:13][S:12][C:11](=S)[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.O1CCCC1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(N(CC)CC)C>[CH3:2][C:1]([NH:5][C:6]([N:8]=[C:9]1[N:10]=[C:11]([N:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]2)[S:12][S:13]1)=[O:7])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 21539244HCID 21539244, compound

Product 1

HCID 54307693HCID 54307693, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A suspension of 2.63 parts of 1-t-butyl-3(-3-thioxo-3H-1,2,4-dithiazol-5-yl)urea and 1.42 parts of methyl iodide in 50 parts of tetrahydrofuran was stirred for 1 hour at room temperature and refluxed with stirring for 1 hour. After cooling to room temperature 3.0 parts of triethylamine and 1.0 parts of N-methyl piperazine were added to the suspension and the mixture was stirred at room temperature overnight. The mixture was filtered to remove triethylamine hydroiodide and the solvent was removed from the filtrate under reduced pressure. The filtrate residue was triturated with water and recrystallized from methanol to afford 1.0 part of the title compound, m.p. 169°-172°.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for 1 hour
  3. additionwere added to the suspension
  4. stirringthe mixture was stirred at room temperature overnight
  5. filtrationThe mixture was filtered
  6. customto remove triethylamine hydroiodide
  7. customthe solvent was removed from the filtrate under reduced pressure
  8. customThe filtrate residue was triturated with water
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e74be62693db4f30ad3e3f120870ad9b
Source dataset
uspto-grants-1976_05
Patent number
US03956303

Reaction notes

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