Tert-Butylamine → ethyl-2-(N-tert-butylsulfamoyl)acetate

HRID 553464

Reaction equation

HRID 553464 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([O:8][C:9]([CH2:11][S:12](Cl)(=[O:14])=[O:13])=[O:10])[CH3:7]>C1COCC1>[CH2:6]([O:8][C:9](=[O:10])[CH2:11][S:12](=[O:14])(=[O:13])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 12225100Ethyl (chlorosulfonyl)acetate

Product 1

HCID 19833529ethyl-2-(N-tert-butylsulfamoyl)acetateYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

tert-Butylamine (7.9 mL, 75 mmol.) was dissolved in 50 mL of THF. The solution was cooled to −20° C. and (ethoxycarbonyl)methanesulfonyl chloride dissolved in 10 mL of THF was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 h. The mixture was filtered, and the filtrate concentrated in vacuo. The residue was purified by column chromatography (PE/EtOAc; 2:1) to afford ethyl-2-(N-tert-butylsulfamoyl)acetate (4.1 g, 43%).

Workup

  1. additionwas added slowly
  2. temperatureto warm to room temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by column chromatography (PE/EtOAc; 2:1)

Sources & evidence

ORD record
ord-794c0450771447b48a4f95417416d507
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Linked notes

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