Hydrochloric Acid → HCID 178424926, compound

HRID 1595454Notes

Reaction equation

HRID 1595454 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH2:12][C:13]#[N:14].C([OH:17])C.[ClH:18]>CCOCC>[ClH:18].[CH3:11][C:4]1[CH:5]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:7]=[C:2]([CH3:1])[C:3]=1[CH2:12][C:13](=[NH:14])[OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15538279HCID 15538279, compound

Product 1

HCID 178424926HCID 178424926, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dimethyl4-isopropylphenylacetonitrile (Example 4c); (0.2 g, 1.07 mmol) in anhydrous ether (20 mL) was added absolute ethanol (0.05 g, 1.07 mmol) and an excess of HCl gas was passed into the solution with cooling in an ice bath. The resulting solution was allowed to stir at 0° C. for 2 hours and kept in a refrigerator for 4 days. The white solid was collected by filtration, washed with ether (2×5 mL) and dried to give 0.12 g (42%) of 2-(2,6-dimethyl-4-isopropylphenyl)acetimidate hydrochloride as a white solid, mp 231-233° C. A solution of ethylenediamine (0.053 g, 0.89 mmol) in absolute ethanol (1 mL) was added to a solution of the imidate hydrochloride (0.12 g, 0.44 mmol) in absolute ethanol (4 mL) cooled at ice-bath temperature. After stirring at 0° C. for 2 hour, the solution was heated at reflux for 20 minutes. The solvent was evaporated and the oily residue was washed with water (2×1 mL) and extracted with methylene chloride (3×10 mL). The solution was dried (MgSO4), filtered and evaporated under reduced pressure to afford the free base of the title compound as a white solid (mp 112-114° C.). A solution of the free base in anhydrous ether was treated with dry HCl gas. The crude salt was collected and recrystallized from ethanol/ether to give 0.08 g (65%) of the title compound as a white solid. mp 296-298° C.; Anal. C15H22N2.HCl.0.1H2O: C, H, N.

Workup

  1. temperaturewith cooling in an ice bath
  2. waitkept in a refrigerator for 4 days
  3. filtrationThe white solid was collected by filtration
  4. washwashed with ether (2×5 mL)
  5. customdried

Sources & evidence

ORD record
ord-d3754836342449a383ffffc18fb34ef2
Source dataset
uspto-grants-2001_09
Patent number
US06288101B1

Reaction notes

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