Dimethylformamide → HCID 54158307, compound

HRID 580760Notes

Reaction equation

HRID 580760 reaction equation
[OH:1][CH:2]([CH2:5][OH:6])[CH2:3][NH2:4].C(N([CH2:12][CH3:13])CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16].[CH3:19]N(C)C=O>ClCCl>[CH3:19][C:12]1([CH3:13])[O:6][CH2:5][CH:2]([CH2:3][NH:4][S:15]([CH3:14])(=[O:17])=[O:16])[O:1]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 735613-Amino-1,2-propanediol

Product 1

HCID 54158307HCID 54158307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

45.56 g (500 mmol) of 2,3-dihydroxypropylamine is introduced in 1000 ml of dimethylformamide. After 50.6 g (500 mmol) of triethylamine is added, 57.28 g (500 mmol) of methanesulfonic acid chloride, dissolved in 500 ml of dichloromethane, is instilled under nitrogen atmosphere at 0° C. Then, it is stirred for 1 hour at 0° C. and for 16 hours at room temperature. After the reaction (TLC control) is completed, it is filtered, and the filtrate is concentrated by evaporation in a vacuum. The residue is mixed with 500 ml of tetrahydrofuran, cooled to 0° C. and again filtered. The filtrate is mixed with 500 ml of tetrahydrofuran, 260 ml of 2,2-dimethoxypropane and 5.2 g of ammonium chloride. The resulting reaction mixture is refluxed for 4 hours, then the solvent is evaporated in a vacuum and the residue is taken up in dichloromethane. It is washed three times with one-percent aqueous citric acid, three times with saturated, aqueous sodium bicarbonate solution and finally three times with water. After the organic phase is dried on sodium sulfate, the solvent is drawn off in a vacuum and the residue is distilled on a bulb tube.

Workup

  1. customis instilled under nitrogen atmosphere at 0° C
  2. customAfter the reaction (TLC control)
  3. filtrationit is filtered
  4. concentrationthe filtrate is concentrated by evaporation in a vacuum
  5. additionThe residue is mixed with 500 ml of tetrahydrofuran
  6. temperaturecooled to 0° C.
  7. filtrationagain filtered
  8. additionThe filtrate is mixed with 500 ml of tetrahydrofuran, 260 ml of 2,2-dimethoxypropane and 5.2 g of ammonium chloride
  9. customThe resulting reaction mixture
  10. temperatureis refluxed for 4 hours
  11. customthe solvent is evaporated in a vacuum
  12. washIt is washed three times with one-percent aqueous citric acid, three times with saturated, aqueous sodium bicarbonate solution and finally three times with water
  13. customAfter the organic phase is dried on sodium sulfate
  14. distillationthe residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-3db29453fbbd4ff7af8cf2705aaf397f
Source dataset
uspto-grants-1999_07
Patent number
US05919431

Reaction notes

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