Methyl vinyl ketone → HCID 21269546, compound

HRID 1194341Notes

Reaction equation

HRID 1194341 reaction equation
[CH2:1]([C:8]1[CH:17]=[CH:16][C:11]2[NH:12][C:13](=[S:15])[NH:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19]([CH:21]=[CH2:22])=[O:20]>>[CH2:1]([C:8]1[CH:17]=[CH:16][C:11]2[N:12]([CH2:22][CH2:21][C:19](=[O:20])[CH3:18])[C:13](=[S:15])[NH:14][C:10]=2[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 21269540HCID 21269540, compound

Product 1

HCID 21269546HCID 21269546, compound

Procedure

16 g (66.7 mmoles) of 5-benzyl-benzimidazoline-2-thione are stirred in 30 ml of methylvinylketone for 25 hours. The excess of the detone is distilled off under vacuum (0.1 to 0.2 bars), 50 ml of isopropanol are poured onto the residue, then the solvent is distilled off. Upon pouring ether onto the residue, crystalls are obtained. These are filtered off, and recrystallized from acetonitrile, then ethanol. The title product thus obtained melts at a temperature of 141°-142° C.

Workup

  1. distillationThe excess of the detone is distilled off under vacuum (0.1 to 0.2 bars), 50 ml of isopropanol
  2. additionare poured onto the residue
  3. distillationthe solvent is distilled off
  4. additionUpon pouring ether onto the residue, crystalls
  5. customare obtained
  6. filtrationThese are filtered off
  7. customrecrystallized from acetonitrile
  8. customat a temperature of 141°-142° C.

Sources & evidence

ORD record
ord-ecb26d32048a47a0918cbe49c437e8ba
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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