Thionyl Chloride → HCID 15225717, compound

HRID 128997Notes

Reaction equation

HRID 128997 reaction equation
O[CH:2]([C:8]1[N:15]2[C:11]([N:12]([CH3:21])[C:13]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=32)=[N:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:7][N:5]([CH3:6])[C:3](=[O:4])[CH2:2][C:8]1[N:15]2[C:11]([N:12]([CH3:21])[C:13]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=32)=[N:10][C:9]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15222251HCID 15222251, compound

Product 1

HCID 15225717HCID 15225717, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.73 g (0.035 mol) of α-Hydroxy-N,N,6,9-tetramethyl-2-phenyl-9H-imidazo[1,2-a]benzimidazole-3-acetamide are treated with 75 ml of thionyl chloride in 250 ml of dichloromethane for 24 h. The solvent is evaporated and the excess thionyl chloride is evaporated under reduced pressure. The residue is taken up in toluene and the mixture is again evaporated. The residue is taken up in 600 ml of dichloromethane, 22 g of Rongalite® are added and the mixture is stirred for 48 h. Insoluble matter is removed by filtration. The filtrate is washed with water, with an aqueous sodium bicarbonate solution and again with water. The organic phase is dried over sodium sulphate, and the solvent is evaporated under reduced pressure. 10.36 g of solid are isolated which are purified by silica gel column chromatography, eluting with a chloroform/methanol 90/10 mixture. 7.86 g of product are isolated of which 1.3 g are removed and dissolved in dichloromethane. The solution is filtered and the filtrate is evaporated under reduced pressure. The residue is treated with carbon black in methanol, the suspension is filtered, the methanol is evaporated under reduced pressure, and the residue is dried under vacuum. 0.9 g of white solid are obtained. Melting point: 222°-223° C.

Workup

  1. customThe solvent is evaporated
  2. customthe excess thionyl chloride is evaporated under reduced pressure
  3. customthe mixture is again evaporated
  4. addition22 g of Rongalite® are added
  5. customInsoluble matter is removed by filtration
  6. washThe filtrate is washed with water, with an aqueous sodium bicarbonate solution and again with water
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-73b3f29245634f5ab9f4e23c386fc892
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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