2-Chloroethanol → HCID 21269545, compound

HRID 1194336Notes

Reaction equation

HRID 1194336 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.[OH-].[Na+].O.Cl[CH2:22][CH2:23][OH:24]>C(O)C>[CH2:1]([C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[C:13]([S:15][CH2:22][CH2:23][OH:24])[NH:14][C:10]=2[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21269540HCID 21269540, compound

Product 1

HCID 21269545HCID 21269545, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.75 g (24 mmoles) of 5-benzyl-benzimidazoline-2-thione, a solution of 1 g of sodium hydroxide and 8 ml of water, 2 ml (30 mmoles) of 2-chloroethanol and 30 ml of ethanol are refluxed for an hour. The reaction mixture is evaporated and extracted with water and dichloromethane, then the aqueous phase is extracted with dichloromethane. The residue of the combined organic phases is solidified under ether. After filtration and crystallization from ethyl acetate 4.63 g (68.1%) of title product are obtained. M.p.: 108°-109° C.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionextracted with water and dichloromethane
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. filtrationAfter filtration and crystallization from ethyl acetate 4.63 g (68.1%) of title product
  5. customare obtained

Sources & evidence

ORD record
ord-86dbda4b3801464a8e5cefecc6774fb8
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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