Iodoethane → HCID 21428663, compound

HRID 437589Notes

Reaction equation

HRID 437589 reaction equation
[CH3:1][C:2]1([CH3:37])[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]([CH2:14][CH2:15][CH2:16][N:17]([CH3:35])[CH2:18][CH2:19][CH2:20][N:21]2[C:30](=[O:31])[C:29]([CH3:33])([CH3:32])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:34])[C:3]1=[O:36].[Na].[CH2:39](I)[CH3:40]>C(O)C>[CH3:1][C:2]1([CH3:37])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:39][CH3:40])=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]([CH2:14][CH2:15][CH2:16][N:17]([CH3:35])[CH2:18][CH2:19][CH2:20][N:21]2[C:30](=[O:31])[C:29]([CH3:32])([CH3:33])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:34])[C:3]1=[O:36]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 5360545SodiumHCID 21428671HCID 21428671, compound

Product 1

HCID 21428663HCID 21428663, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.3 gm of N-[3-(3,4-dihydro-4,4-dimethyl-7-hydroxy-1,3-dioxo-2(1H)-isoquinolyl)-propyl]-N-[3-(3,4-dihydro-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolyl)-propyl]-methylamine were dissolved in 10 ml of absolute ethanol, the resulting solution was added to a solution of 0.06 gm of sodium in 10 ml of absolute ethanol, and 0.42 gm of ethyl iodide was added to the mixed solution. The mixture was refluxed for 30 minutes, another 0.42 gm of ethyl iodide was added, and the mixture was refluxed again for 30 minutes. The product was purified on a silicagel column (eluant: chloroform/ethanol = 25:1), and the hydrochloride was precipitated from acetone with ethereal hydrochloric acid. The hydrochloride sintered above 45° C; yield: 0.5 gm (35% of theory).

Workup

  1. additionwas added to the mixed solution
  2. temperatureThe mixture was refluxed for 30 minutes
  3. temperaturethe mixture was refluxed again for 30 minutes
  4. customThe product was purified on a silicagel column (eluant: chloroform/ethanol = 25:1)
  5. customthe hydrochloride was precipitated from acetone with ethereal hydrochloric acid
  6. customThe hydrochloride sintered above 45° C

Sources & evidence

ORD record
ord-250868536a51468cb0b3dcbfa2dc3538
Source dataset
uspto-grants-1977_06
Patent number
US04031219

Reaction notes

Loading…