Thionyl Chloride → HCID 57785791, compound

HRID 1399254Notes

Reaction equation

HRID 1399254 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]([NH2:26])=O)=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]#[N:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 57785904HCID 57785904, compound

Product 1

HCID 57785791HCID 57785791, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamide (850 mg 2.07 mmol) in N,N-dimethylformamide (10 mL) was added thionyl chloride (0.448 mL, 6.21 mmol). The resultant mixture was stirred at 50° C. for 30 min and poured into saturated aqueous sodium hydrogen carbonate at 0° C. The resultant precipitate was collected by filtration, washed with water and diisopropyl ether to give the title compound as a colorless solid (532 mg, 1.39 mmol, 67%).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with water and diisopropyl ether

Sources & evidence

ORD record
ord-88c7f2399d314656ba7c0456dbfdb5b5
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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