Hydrochloric Acid → HCID 178429016, compound

HRID 1154003Notes

Reaction equation

HRID 1154003 reaction equation
[ClH:1].C([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([NH:17][C:18]([NH:20][C:21](=[NH:23])[NH2:22])=[O:19])=[C:12]([CH3:24])[CH:11]=1)C1C=CC=CC=1.Cl.[H][H]>[Pd].C(O)C>[ClH:1].[OH:9][C:10]1[CH:11]=[C:12]([CH3:24])[C:13]([NH:17][C:18]([NH:20][C:21](=[NH:22])[NH2:23])=[O:19])=[C:14]([CH3:16])[CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178428945HCID 178428945, compound

Product 1

HCID 178429016HCID 178429016, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-benzyloxy-2,6-dimethylphenyl)-3-amidinourea hydrochloride (7.0 g), methanolic HCl (50 ml), 5% Pd/C (1.0 g) and 150 ml of absolute ethanol are shaken under an atmosphere of H2 (50 psi) until the uptake of hydrogen ceases. The mixture is filtered through a pad of Celite and the pad washed well with methanol. The filtrate is concentrated under vacuo and the residue crystallized from methanol/acetonitrile to give, after filtering and vacuum drying, 4.7 grams of an off-white solid, M.P. 204°-206° C. Recrystallization from methanol/acetonitrile gave, after filtering and vacuum drying, 2.3 grams, M.P. 208°-210° C. of the hydrochloride salt.

Workup

  1. filtrationThe mixture is filtered through a pad of Celite
  2. washthe pad washed well with methanol
  3. concentrationThe filtrate is concentrated under vacuo
  4. customthe residue crystallized from methanol/acetonitrile
  5. customto give
  6. filtrationafter filtering
  7. customvacuum drying
  8. customRecrystallization from methanol/acetonitrile
  9. customgave
  10. filtrationafter filtering
  11. customvacuum drying

Sources & evidence

ORD record
ord-8cf8717664b24cf4a02c00f7751c3b51
Source dataset
uspto-grants-1984_12
Patent number
US04487779

Reaction notes

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