Triethylamine → HCID 15896077, compound

HRID 842985Notes

Reaction equation

HRID 842985 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:21])[CH2:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:9].[S:22](Cl)([Cl:25])(=[O:24])=[O:23]>C(Cl)Cl>[CH2:14]([N:13]([S:22]([Cl:25])(=[O:24])=[O:23])[CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 15896077HCID 15896077, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (2.0 ml, 14.4 mmol) and N-benzylglycine ethyl ester (2.25 ml, 12.0 mmol) in methylene chloride (5 ml) was added to a solution of sulfuryl chloride (0.96 ml, 12.0 mmol) in methylene chloride (30 ml) at −78° C. The reaction mixture was stilted at −78° C. for 4 h and then concentrated. Ether (75 ml) was added and the resulting precipitate was filtered. The organic layer was washed with 1M HCl and brine, dried over MgSO4 and concentrated in vacuo to give ethyl 2-[benzyl-(chlorosulfonyl)amino]acetate as a colorless oil (69%).

Workup

  1. concentrationconcentrated
  2. additionEther (75 ml) was added
  3. filtrationthe resulting precipitate was filtered
  4. washThe organic layer was washed with 1M HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-544d7d59a2dc40bba0059894b76494be
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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