Hydrochloric Acid → HCID 131714379, compound

HRID 464380Notes

Reaction equation

HRID 464380 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17](C#N)=[CH:16][C:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][N:13]=1.[ClH:25].[C:26](=[O:29])([O-])[O-:27].[Na+].[Na+]>O>[ClH:25].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:26]([OH:27])=[O:29])=[CH:16][C:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][N:13]=1.[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:26]([OH:27])=[O:29])=[CH:16][C:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 20212019HCID 20212019, compound

Product 1

HCID 131714379HCID 131714379, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-3-cyano-5-n-pentylpyridine obtained above (2.53 g; 0.0074 moles) was treated with conc. hydrochloric acid (20 ml) and heated to reflux for 36 hours. After stripping the mixture to dryness, the residue was dissolved in a little water and basified to about pH6 with sodium carbonate solution giving a precipitate. The mixture was azeotroped to dryness and chromatographed on silica-gel using chloroform/ethanol (20:1) to collect the desired band. The 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-5-n-pentylpyridine-3-carboxylic acid hemihydrochloride obtained (1.25 g) could not be crystallised and it was a straw-coloured glass. NMR data (DMSO-d6): --CH3CH2 at 0.88; (CH2)3 at 1.1-1.7; Im-CH3 at 2.24; pyr-CH2 at 2.47; CH2CH2S at 2.70; NCH2CH2 at 3.64; ImCH2S at 3.82; pyr-4H at 7,93; pyr-6H at 8.12 and Im-2H at 8.40.

Workup

  1. temperatureheated
  2. temperatureto reflux for 36 hours
  3. customgiving a precipitate
  4. customThe mixture was azeotroped to dryness
  5. customchromatographed on silica-gel
  6. customto collect the desired band

Sources & evidence

ORD record
ord-13164b75852c4f41ad33cb27245ed563
Source dataset
uspto-grants-1985_10
Patent number
US04547512

Reaction notes

Loading…