Triethylamine → HCID 66817509, compound

HRID 1754926Notes

Reaction equation

HRID 1754926 reaction equation
Br[CH2:2][CH2:3][OH:4].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[CH2:12]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH3:13].C(N(CC)CC)C>ClCCl>[CH2:12]([C:14]1[CH:15]=[C:16]([NH:17][S:6]([N:9]2[CH2:2][CH2:3][O:4][C:10]2=[O:11])(=[O:8])=[O:7])[CH:18]=[CH:19][CH:20]=1)[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 114753-EthylanilineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 66817509HCID 66817509, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Bromoethanol (0.28 mL, 4.00 mmol) was added to a solution of chlorosulfonyl isocyanate (0.35 mL, 4.00 mmol) in dichloromethane (1.8 mL) at 0° C. After stirring for 90 minutes, a solution of 3-ethylaniline (0.55 mL, 4.40 mmol) and triethylamine (1.23 mL, 8.80 mmol) in dichloromethane (3.6 mL) was added. The mixture was stirred for 90 minutes and then quenched with a 2 N aqueous hydrochloric acid solution. The mixed solution was separated, and the aqueous layer was then extracted with ether. The organic layers were combined and washed with water and saturated brine, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was washed with ether (5 mL) to give 2-oxo-oxazolidine-3-sulfonic acid (3-ethylphenyl)amide (LCMS yield 80%).

Workup

  1. stirringThe mixture was stirred for 90 minutes
  2. customquenched with a 2 N aqueous hydrochloric acid solution
  3. customThe mixed solution was separated
  4. extractionthe aqueous layer was then extracted with ether
  5. washwashed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting residue was washed with ether (5 mL)

Sources & evidence

ORD record
ord-c30b0c58ff994b0e833ae724771c3cf9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…