2-Chloroethanol → HCID 67485759, compound

HRID 1809606Notes

Reaction equation

HRID 1809606 reaction equation
Cl[CH2:2][CH2:3][OH:4].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].C(N(CC)CC)C>ClCCl>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH:16][S:6]([N:9]1[CH2:2][CH2:3][O:4][C:10]1=[O:11])(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 8471Triethylamine2×HCID 66053N,N-DimethylethylenediamineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 67485759HCID 67485759, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-chloroethanol (2.00 g, 24.84 mmol) in dichloromethane (15 mL) was added to a solution of chlorosulfonyl isocyanate (3.52 g, 24.8 mmol) in dichloromethane (15 mL) This mixture was slowly added to a 0° C. solution of N1,N1-dimethylethane-1,2-diamine (2.19 g, 24.8 mmol) and triethylamine (3.81 mL, 27.3 mmol). The reaction was stirred for 45 minutes, diluted with dichloromethane, washed with saturated ammonium chloride, concentrated and purified by silica gel chromatography. The isolated material was dissolved in methylene chloride and triethylamine (3.81 mL, 27.3 mmol) and stirred for 5 hours. The reaction mixture was washed with water and the organic layer was concentrated to give crude N-(2-(dimethylamino)ethyl)-2-oxooxazolidine-3-sulfonamide (3.96 g, 67.24% yield).

Workup

  1. washwashed with saturated ammonium chloride
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography
  4. dissolutionThe isolated material was dissolved in methylene chloride
  5. washThe reaction mixture was washed with water
  6. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-eca573f7320245a983de5b2d9b3da26b
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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