Triethylamine → N-cyclopropyl-2-oxooxazolidine-3-sulfonamide

HRID 64062Notes

Reaction equation

HRID 64062 reaction equation
Br[CH:2]([OH:4])[CH3:3].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH:12]1([NH:15][S:6]([N:9]2[CH2:3][CH2:2][O:4][C:10]2=[O:11])(=[O:8])=[O:7])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 70918Chlorosulfonyl isocyanateHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 89500324N-cyclopropyl-2-oxooxazolidine-3-sulfonamideYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of bromoethanol (1 g, 8.06 mmol) in DCM was added chloro sulfonyl isocyanate (1.13 g, 8.06 mmol) in DCM and this solution added over 2 min, dropwise, to cyclopropyl amine (0.552 g, 0.009 mmol) and triethylamine (1 ml, 0.007 mmol) in DCM and stirred at RT for 1 h. The mixture was quenched with 0.2 M HCl solution and extracted with DCM (3×150 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 48% yield (0.8 g). 1H NMR (400 MHz, DMSO-d6): δ 8.15-8.14 (d, 1H), 4.42 (t, 2H), 3.70 (t, 2H), 2.35 (m, 1H), 0.58-0.53 (m, 4H).

Workup

  1. additionthis solution added over 2 min
  2. customThe mixture was quenched with 0.2 M HCl solution
  3. extractionextracted with DCM (3×150 ml)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulphate
  6. distillationThe solvent was distilled off
  7. customto afford the product in 48% yield (0.8 g)

Sources & evidence

ORD record
ord-e4a97856d825493392efda217da6f8e0
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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