Sodium Hydroxide → HCID 13343778, compound

HRID 1903140Notes

Reaction equation

HRID 1903140 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[C:3]1=[CH:4][C:5]1[N:9]=[C:8]([SH:10])[NH:7][C:6]=1[CH:11]=2.[OH-].[Na+].Cl.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>O>[CH3:1][C:2]1([CH3:18])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[C:3]1=[CH:4][C:5]1[N:9]=[C:8]([S:10][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[NH:7][C:6]=1[CH:11]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178424890HCID 178424890, compound

Product 1

HCID 13343778HCID 13343778, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.0 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-naphth(2,3-d)imidazole-2-thiol were suspended in 60 ml of alcohol in a 250 ml sulfonation flask equipped with stirrer, thermometer, dropping funnel and reflux condenser. A solution of 3.24 g of sodium hydroxide in 20 ml of water was added dropwise thereto while stirring well and the mixture was stirred at room temperature for an additional 30 minutes. After adding 6.0 g of 2-chloromethyl-pyridine hydrochloride, the mixture was boiled at reflux overnight and subsequently evaporated. The residue was taken up in 1 l of ethyl acetate, washed neutral three times with 250 ml of water, dried over sodium sulfate and, after evaporation in vacuo, recrystallized from acetonitrile. There were obtained 7.0 g (57.3% of theory) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-[(2-pyridylmethyl)thio]-1H-naphth(2,3-d)-imidazole of melting point 199°-200° C.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. stirringthe mixture was stirred at room temperature for an additional 30 minutes
  4. temperatureat reflux overnight
  5. customsubsequently evaporated
  6. washwashed neutral three times with 250 ml of water
  7. dry with materialdried over sodium sulfate
  8. customafter evaporation in vacuo
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c6b298b5a5f440a48a696f7c26c65e2a
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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