Iodoethane → HCID 21191829, compound

HRID 399775Notes

Reaction equation

HRID 399775 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:14])[O:12][CH3:13].[CH2:15](I)[CH3:16]>CN(C)C=O>[CH2:15]([N:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH3:3])[C:11](=[O:14])[O:12][CH3:13])[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 519038CARBAMIC ACID, (2-METHYLPHENYL)-, METHYL ESTER

Product 1

HCID 21191829HCID 21191829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 g (0.2 mol) of sodium hydride are added a little at a time to 30 g (0.18 mol) of methyl N-(o-methylphenyl)-carbamate (Example 1a) in 200 ml of dimethylformamide. After the evolution of gas has ceased, 30 g (0.2 mol) of ethyl iodide are added drop-wise, the reaction mixture being lightly cooled in a water bath. A white solid is precipitated. After about 4 hours, the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether. The organic phase is dried over MgSO4 and evaporated down. The residue is distilled. 32.5 g (0.17 mol=93%) of the title compound are obtained as a colorless oil. bp.0.5 =74° C.; 1H-NMR (CDCl3 ; δ (ppm): 7.2 (m, 3H, aromatic); 7.1 (m, 1H, aromatic); 3.8 (m, 1H, N--CHA); 3.6 (s, 3H, OCH3); 3.5 (m, 1H, N--CHB); 2.2 (s, 3H, CH3); 1.1 (t, 3H, CH3)

Workup

  1. temperaturethe reaction mixture being lightly cooled in a water bath
  2. customA white solid is precipitated
  3. additionthe reaction mixture is diluted with water
  4. extractionthe aqueous phase is extracted three times with ether
  5. dry with materialThe organic phase is dried over MgSO4
  6. customevaporated down
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-3782cf1a5aee4b74bbd6cfca1b433bc8
Source dataset
uspto-grants-1998_10
Patent number
US05824705

Reaction notes

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