Iodoethane → HCID 135969006, compound

HRID 609890Notes

Reaction equation

HRID 609890 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=S)[C:20]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=1)[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1.[H-].[Na+].C(I)C.[N:41]#[C:42][NH2:43]>O1CCCC1>[C:42]([NH:43][C:19](=[N:18][CH2:17][CH2:16][CH2:15][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1)[C:20]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=1)#[N:41]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 9864CyanamideHCID 24758Sodium hydrideHCID 136076830HCID 136076830, compound

Product 1

HCID 135969006HCID 135969006, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[3-[N-methyl-N-[2-(3,4-methylenedioxyphenoxy)ethyl]amino]propyl]-3,5-di-tert-butyl-4-hydroxybenzothioamide (1.0 g) obtained in Example 60 in dry tetrahydrofuran was added sodium hydride (0.16 g) at 0° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 1 hour. To the mixture was added ethyl iodide (0.31 g), followed by stirring at room temperature for 2 hours. The mixture was again cooled to 0° C., and cyanamide (0.84 g) was added thereto, followed by stirring at room temperature for 15 hours. After completion of the reaction, the mixture was poured into ice-water, and the product was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 99:1) to afford 0.70 g (69%) of the title compound as pale yellow crystals. mp 129-130° C. NMR (CDCl3) (200 MHz) δ: 1.45 (18H, s), 1.6-2.1 (2H, m), 2.20 (3H, s), 2.6-3.0 (4H, m), 3.6-3.8 (2H, m), 3.83 (2H, t, J=5.7 Hz), 5.56 (1H, s), 5.84 (2H, s), 5.8-6.8 (3H, m), 7.48 (2H, s), 8.44 (1H, brs)

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. stirringby stirring at room temperature for 15 hours
  3. customAfter completion of the reaction
  4. extractionthe product was extracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 99:1)

Sources & evidence

ORD record
ord-d6dd57c83fba4a27bee90f84deee1572
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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