Methyl iodide → HCID 11084766, compound

HRID 373317Notes

Reaction equation

HRID 373317 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(N(CC)CC)C.[C:15](=[S:17])=[S:16].[CH3:18]I>C(O)C.O>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:15](=[S:17])[S:16][CH3:18]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 11084766HCID 11084766, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 21 g (0.2 mole) of aminoacetaldehyde dimethylacetal in 150 ml of ethanol and 10 ml of water was added 24.3 g (0.24 mole) of triethylamine, and 16.8 g (0.22 mole) of carbon disulfide in portions at 0° to 5° C. After the reaction mixture was stirred for one hour at the same temperature, 31.2 g (0.22 mole) of methyl iodide was added dropwise in portions, and then was further stirred for one hour at 15°±5° C. The solvent was removed under reduced pressure (30 mmHg) and water was added thereto. Then, the mixture was extracted with ethylacetate, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure (30 mmHg) to obtain the desired liquid compound, 36.9 g (yield 95%).

Workup

  1. additionwas added dropwise in portions
  2. customThe solvent was removed under reduced pressure (30 mmHg) and water
  3. additionwas added
  4. extractionThen, the mixture was extracted with ethylacetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure (30 mmHg)
  8. customto obtain the desired liquid compound, 36.9 g (yield 95%)

Sources & evidence

ORD record
ord-d6d8d77b3b72484485344f07974a142c
Source dataset
uspto-grants-1992_11
Patent number
US05162534

Reaction notes

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