Sodium Bicarbonate → HCID 21269560, compound

HRID 1194331Notes

Reaction equation

HRID 1194331 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.[ClH:18].[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][Cl:23].C(=O)([O-])O.[Na+]>CO>[ClH:23].[ClH:18].[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][S:15][C:13]1[NH:14][C:10]2[CH:9]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:17]=[CH:16][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 21269540HCID 21269540, compound

Product 1

HCID 21269560HCID 21269560, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the method described in Example 2 g (25 mmoles) of 5-benzyl-benzimidazoline-2-thione, 4.32 g (30 mmoles) of 2-(dimethylamino)-ethylchloride hydrochloride and 2.55 g of sodium hydrogencarbonate are refluxed in methanol. The salt is filtered off, the filtrate is concentrated and treated with aqueous sodium hydroxide solution and dichloromethane. The organic phase is separated, concentrated and the salt is precipitated by adding hydrochloric ether. 8.15 g (84.8%) of 2-(2-dimethylaminoethylthio)-5-benzyl-benzimidazole dihydrochloride are obtained, which melts at 204° C. after recrystallization from isopropanol.

Workup

  1. filtrationThe salt is filtered off
  2. concentrationthe filtrate is concentrated
  3. additiontreated with aqueous sodium hydroxide solution and dichloromethane
  4. customThe organic phase is separated
  5. concentrationconcentrated
  6. customthe salt is precipitated
  7. additionby adding hydrochloric ether

Sources & evidence

ORD record
ord-cb38a36b8ae442bfb409a4aeb7102357
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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