Ethanolamine → HCID 71437973, compound

HRID 2400932Notes

Reaction equation

HRID 2400932 reaction equation
[CH3:1][O:2][C:3](=[N:5][S:6]([N+:9](CC)(CC)[CH2:10][CH3:11])(=[O:8])=[O:7])[O-:4].NCCO>C1COCC1>[CH3:1][O:2][C:3]([N:5]1[CH2:11][CH2:10][NH:9][S:6]1(=[O:8])=[O:7])=[O:4]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate

Product 1

HCID 71437973HCID 71437973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methoxy-N-triethylammoniosulfonylmethanimidate (Burgess reagent, 12.3 mmol) in THF (10 mL) at 0° C. was added 2-aminoethanol (4.91 mmol). The reaction was allowed to warm to rt and then heated to 90° C. for 8 h. After cooling to rt, the reaction was quenched with saturated aq. NH4Cl. The mixture was extracted with EtOAc and the organic layer was dried (Na2SO4) and concentrated to afford 1,1-dioxo-1λ6-[1,2,5]thiadiazolidine-2-carboxylic acid methyl ester as colorless oil that was used without further purification.

Workup

  1. temperatureheated to 90° C. for 8 h
  2. temperatureAfter cooling to rt
  3. customthe reaction was quenched with saturated aq. NH4Cl
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b16cbebb8f624191bdcda517849eacc7
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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