HCID 19373119, compound → HCID 15222250, compound

HRID 129003Notes

Reaction equation

HRID 129003 reaction equation
O[CH:2]([C:8]1[N:15]2[C:11]([N:12]([CH3:22])[C:13]3[CH:19]=[C:18]([CH3:20])[C:17]([CH3:21])=[CH:16][C:14]=32)=[N:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]>ClCCl>[CH3:7][N:5]([CH3:6])[C:3](=[O:4])[CH2:2][C:8]1[N:15]2[C:11]([N:12]([CH3:22])[C:13]3[CH:19]=[C:18]([CH3:20])[C:17]([CH3:21])=[CH:16][C:14]=32)=[N:10][C:9]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 19373119HCID 19373119, compound

Product 1

HCID 15222250HCID 15222250, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.7 g (0.0363 mol) of α-hydroxy-N,N,6,7,9-pentamethyl-2-phenyl-9H-imidazo[1,2-a]benzimidazole-3-acetamide are dissolved in 500 ml of dichloromethane. A slight insoluble matter is removed by filtration. 75 ml of thionyl chloride are added to the filtrate and the mixture is stirred for 3 h, allowed to stand overnight, and again stirred for 6 h. The solvent is evaporated under reduced pressure, as well as the excess thionyl chloride by means of toluene. The residue is dissolved in 500 ml of dichloromethane and 23.5 g of Rongalite® are added to this solution. The mixture is stirred for 48 h. The insoluble matter is removed by filtration, and the organic phase is washed with water, with sodium bicarbonate solution and then with water. It is dried over sodium sulphate and concentrated under reduced pressure. 12.23 g of product are obtained which are washed with ether and then purified by silica gel column chromatography, eluting with a chloroform/acetone 95/5 mixture. 6.16 g of product are obtained, of which 1.32 g are removed for two successive treatments with carbon black in methanol. 1.04 g of product are finally isolated. Melting point: 202°-206° C.

Workup

  1. customA slight insoluble matter is removed by filtration
  2. addition75 ml of thionyl chloride are added to the filtrate
  3. waitto stand overnight
  4. stirringagain stirred for 6 h
  5. customThe solvent is evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in 500 ml of dichloromethane
  7. addition23.5 g of Rongalite® are added to this solution
  8. stirringThe mixture is stirred for 48 h
  9. customThe insoluble matter is removed by filtration
  10. washthe organic phase is washed with water, with sodium bicarbonate solution
  11. dry with materialIt is dried over sodium sulphate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f483c67812144bd9a27ecade525043f
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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