Sodium Thiosulfate → 9-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfonyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1628971Notes

Reaction equation

HRID 1628971 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23]SCC)=[CH:4][CH:3]=1.Cl[C:28]1C=CC=C(C(OO)=O)[CH:29]=1.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23][S:38]([CH2:28][CH3:29])(=[O:42])=[O:40])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 577863759-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Product 1

HCID 577859309-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfonyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (216 mg, 0.506 mmol) in acetonitrile (10 mL) was added 3-chloroperbenzoic acid (70%, 0.274 g, 1.11 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr. Aqueous sodium thiosulfate was added to the reaction mixture at 0° C. and the mixture was stirred at room temperature. The mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate and brine. The organic layer was concentrated in vacuo and the precipitated solid was collected by filtration. The solid was washed with water, 2-propanol and diisopropyl ether to give the title compound (190 mg, 0.414 mmol, 82%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate and brine
  4. concentrationThe organic layer was concentrated in vacuo
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe solid was washed with water, 2-propanol and diisopropyl ether

Sources & evidence

ORD record
ord-b851294259ee488282630e2162dfc22c
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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