Triethylamine → tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamate

HRID 1405944Notes

Reaction equation

HRID 1405944 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([NH:1][CH2:2][CH2:3][NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47454467tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamateYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 1000 ml reaction flask, 36.9 g of tert-butyl 2-aminoethylaminoformate and 200 ml of dichloromethane were added. The mixture was stirred by an electromagnetic stirrer, cooled with ice-bath, added with 96 ml of triethylamine, slowly added dropwise with 35.9 g of methylsulfonyl chloride in 200 ml of dichloromethane. The temperature of the mixture was naturally warmed to room temperature and the mixture was conducted overnight. The mixture was added dropwise with ice-water to quench reaction, the organic layer was separated, and the water layer was extracted with dichloromethane. The organic layers were combined, washed sequentially with 5 mol/L dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtrated, and distilled under a reduced pressure to remove the solvent to obtain 28.6 g of brown yellow solid, yield 52.1%.

Workup

  1. additionwere added
  2. temperaturecooled with ice-bath
  3. customto quench
  4. customreaction
  5. customthe organic layer was separated
  6. extractionthe water layer was extracted with dichloromethane
  7. washwashed sequentially with 5 mol/L dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltrated
  10. distillationdistilled under a reduced pressure
  11. customto remove the solvent

Sources & evidence

ORD record
ord-47b84698531f4ba6a63e3990ed3bef92
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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