Hydrochloric Acid → HCID 21273251, compound

HRID 1382778Notes

Reaction equation

HRID 1382778 reaction equation
[CH3:1][N:2]([CH3:32])[C:3](=[O:31])/[CH:4]=[CH:5]/[C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]=1[CH3:11].[ClH:33].CCOCC>C(O)C.[Pd]=O>[ClH:33].[ClH:33].[CH3:32][N:2]([CH3:1])[C:3](=[O:31])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21273233HCID 21273233, compound

Product 1

HCID 21273251HCID 21273251, compound

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent2×

Procedure

A solution of (E)-N,N-dimethyl-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propenamide (6.0 g) in ethanol (100 ml) was hydrogenated at room temperature and pressure over 10% palladium oxide on carbon (dry, 2.0 g, pre-reduced in ethanol (25 ml)) for 48 h. The catalyst was filtered off (Hyflo), replaced with fresh palladium oxide (2.0 g) and hydrogenation continued for 72 h. The catalyst was filtered off (Hyflo) and the filtrate evaporated in vacuo to yield a yellow oil. This was dissolved in ethanol (15 ml) and acidified with ethanolic hydrogen chloride (to pH1). Dry ether (500 ml) was added and the resulting precipitate was filtered off to give the title compound (1.72 g) as a white powder, m.p. 142°-144°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off (Hyflo)
  3. filtrationThe catalyst was filtered off (Hyflo)
  4. customthe filtrate evaporated in vacuo
  5. customto yield a yellow oil
  6. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-16adf2658a18475fbdb64fd1b67ed8d1
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

Loading…