Methyl iodide → HCID 19802541, compound

HRID 1645910Notes

Reaction equation

HRID 1645910 reaction equation
[H-].[Na+].O[C:4]1[C:13](O)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][NH:8][C:9]2=[S:15].[CH3:16]I>CCCCCC.C1COCC1.CCOCC>[CH3:16][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][NH:8][C:9]2=[S:15]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136066327HCID 136066327, compound

Product 1

HCID 19802541HCID 19802541, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To 0.15 g of 60% sodium hydride (3.70 mmol) which was washed with n-hexane and suspended in 15 ml of THF was added dropwise at 0 a solution of 0.50 g (2.82 mmol) of 3,4-dihydro-5,6-dihydroxy-1(2H)-isoquinolinethione in 5 ml of THF. The thick white suspension which formed was stirred for 0.5 hours at 0°-5° and then 0.45 g (2.82 mmol) of methyl iodide in 5 ml THF was added and stirring continued for one hour. The resulting yellow solution was diluted with ether, washed with saturated NaCl, dried (Na2SO4), and concentrated. The resulting oil was recrystallized from 1 ml of n-hexane to give pale yellow crystals, 0.55 g (100%); mp 43°-45°.

Workup

  1. customThe thick white suspension which formed
  2. stirringstirring
  3. waitcontinued for one hour
  4. washwashed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting oil was recrystallized from 1 ml of n-hexane
  8. customto give pale yellow crystals, 0.55 g (100%)

Sources & evidence

ORD record
ord-dc80ec97d5384553a6f62ed1f3627a19
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

Loading…