Sodium Bicarbonate → HCID 21269532, compound

HRID 1194333Notes

Reaction equation

HRID 1194333 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[S:9])[NH:8][C:4]=2[CH:3]=1.Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][S:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7123736-Methyl-1H-benzimidazole-2-thiolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 21269532HCID 21269532, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.11 g (25 mmoles) of 5-methyl-benzimidazoline-2-thione, 4.32 g (30 mmoles) of 2-(dimethylamino)-ethylchloride hydrochloride and 2.55 g of sodium hydrogencarbonate are refluxed in 50 ml of ethanol for 6 hours. The reaction mixture is filtered off, concentrated and the residue is worked up according to the method of Example 2. The dichloromethane extracts are concentrated and the residue is crystallized from petrolether. 3.81 g of 2-(2-dimethylamino-ethylthio)-5-methyl-benzimidazole are obtained, which melting point does not change after recrystallizaton from acetonitrile. M.p.: 103° C.

Workup

  1. filtrationThe reaction mixture is filtered off
  2. concentrationconcentrated
  3. concentrationThe dichloromethane extracts are concentrated
  4. customthe residue is crystallized from petrolether

Sources & evidence

ORD record
ord-699866538c9c49b1ae65fee42df3ed6d
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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