HCID 14520339, compound → HCID 178477816, compound

HRID 1194385Notes

Reaction equation

HRID 1194385 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([C:14]2[N:15]=[CH:16][N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=2)O)[C:5]2[O:6][CH2:7][O:8][CH2:9][C:4]=2[CH:3]=1>C(O)(=O)C.[Pd]>[ClH:1].[O:6]1[C:5]2[C:10]([CH2:12][C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)=[CH:11][CH:2]=[CH:3][C:4]=2[CH2:9][O:8][CH2:7]1

Participants

4

Reactant 1

HCID 14520339HCID 14520339, compound

Product 1

HCID 178477816HCID 178477816, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

50.85 g (0.1 mole) of alpha-(6-chloro-4H-1,3-benzodioxin-8-yl)-1-triphenylmethyl-1H-imidazole-4-methanol (prepared in Example 1.C.1.), dissolved in 500 ml of acetic acid, are hydrogenolyzed in the presence of 3 g of 10% palladium on carbon for 2 hours at 80° C., under a hydrogen pressure of 2.41 bars. The catalyst is then filtered off and the solvent is distilled under reduced pressure. The residue obtained is extracted three times with diethyl ether to remove the triphenylmethane formed. It is subsequently recrystallized from 50 ml of acetonitrile. 21.2 g of 4-[(4H-1,3-benzodioxin-8-yl)methyl]-1H-imidazole hydrochloride are obtained. Yield: 83% of theory; M.P.: 168°-173° C.

Workup

  1. filtrationThe catalyst is then filtered off
  2. distillationthe solvent is distilled under reduced pressure
  3. customThe residue obtained
  4. extractionis extracted three times with diethyl ether
  5. customto remove the triphenylmethane
  6. customformed
  7. customIt is subsequently recrystallized from 50 ml of acetonitrile

Sources & evidence

ORD record
ord-9e3cdc6883f5442790e551ffceef9bc5
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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