Sodium Hydroxide → HCID 13343798, compound

HRID 1903163Notes

Reaction equation

HRID 1903163 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:4]=2[N:3]=[C:2]1[SH:13])[CH2:10][CH2:9][CH2:8]3.[OH-].[Na+].Cl.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24]Cl)=[N:22][CH:23]=1>O>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][S:13][C:2]2[NH:3][C:4]3[CH:12]=[C:11]4[C:7](=[CH:6][C:5]=3[N:1]=2)[CH2:8][CH2:9][CH2:10]4)=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 178527749HCID 178527749, compound

Product 1

HCID 13343798HCID 13343798, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 13.5 g of 1,5,6,7-tetrahydroindeno(5,6-d)imidazole-2-thiol, suspended in 200 ml of alcohol, were added dropwise while stirring 5.9 g of sodium hydroxide in 100 ml of water and, after 30 minutes, 13.0 g of 5-methyl-2-chloromethyl-pyridine hydrochloride were added. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in methylene chloride. This was washed neutral and, after drying over sodium sulfate, evaporated in vacuo. The residue, recrystallized from acetonitrile, gave 11.9 g (56.9% of theory) of 1,5,6,7-tetrahydro-2-[[(5-methyl-2-pyridyl)methyl]thio]indeno(5,6-d)imidazole of melting point 157°-158° C.

Workup

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customevaporated
  5. washThis was washed neutral
  6. dry with materialafter drying over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue, recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2eff22aff2ec401caa884175d8872c11
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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