2-Chloroethyldiisopropylammonium chloride → HCID 21269553, compound

HRID 1194330Notes

Reaction equation

HRID 1194330 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.[CH:13]([N:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][CH2:18]Cl)([CH3:15])[CH3:14].C(=O)([O-])O.[Na+]>C(O)C>[CH:13]([N:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][CH2:18][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)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 516892Sodium BicarbonateHCID 7123736-Methyl-1H-benzimidazole-2-thiol

Product 1

HCID 21269553HCID 21269553, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.16 g (37.5 mmoles) of 5-methyl-benzimidazoline-2-thione, 9 g (45 mmoles) of 2-(diisopropylamino)-ethylchloride hydrochloride and 3.52 g (41.9 mmoles) of sodium hydrogencarbonate are refluxed in 60 ml of ethanol for 6 hours. After the filtration of the salt and concentration of the filtrate the residue is extracted with dichloromethane and aqueous sodium hydroxide solution as described in Example 2. The aqueous phase is further extracted with dichloromethane, the combined organic phases are concentrated, the residue is recrystallized from 47 ml of ethylacetate. The title product thus obtained weights 6.65 g (61%) and melts at 109°-110° C.

Workup

  1. filtrationAfter the filtration of the salt and concentration of the filtrate the residue
  2. extractionis extracted with dichloromethane and aqueous sodium hydroxide solution
  3. extractionThe aqueous phase is further extracted with dichloromethane
  4. concentrationthe combined organic phases are concentrated
  5. customthe residue is recrystallized from 47 ml of ethylacetate

Sources & evidence

ORD record
ord-beef8df9001c45d1a24247de0ea5fed7
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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