Methyl iodide → HCID 22350957, compound

HRID 747538Notes

Reaction equation

HRID 747538 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[CH3:20]I.C(=O)([O-])O.[Na+].[C:27](=[S:29])=[S:28]>O1CCCC1>[CH3:20][S:28][C:27]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[S:29]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 22350957HCID 22350957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of t-butyl 3-aminopropylcarbamate (6 g) and triethylamine (5.03 ml) in tetrahydrofuran (10 ml) was added dropwise carbon disulfide (2.07 ml), and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture was added dropwise methyl iodide (2.14 ml), and the mixture was stirred at room temperature for 0.5 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (11 g) as crude oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 0.5 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-efa0e45b4d554981a9d264afeb8c754f
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

Loading…