Hydrochloric Acid → HCID 54031092, compound

HRID 1195321Notes

Reaction equation

HRID 1195321 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][C:16]([OH:18])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)(Cl)=O.[OH-].[Na+].[NH2:25][CH2:26][C:27]([OH:29])=[O:28].Cl>C1C=CC=CC=1.O.O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][C:16]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 22367151HCID 22367151, compound

Product 1

HCID 54031092HCID 54031092, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1.4 g of [{(1,3-benzodioxol-5-yl)butyl}thio]acetic acid was dissolved in 10 ml of benzene, followed by the addition of 0.8 ml of thionyl chloride. The obtained mixture was heated under reflux for 1.5 hours and concentrated in a vacuum to obtain a residue. Separately, 0.43 g of sodium hydroxide was dissolved in 4 ml of water, followed by the addition of 0.8 g of glycine to obtain a mixture. The above residue was dissolved in a small amount of tetrahydrofuran to obtain a solution. This solution was dropwise added to the above mixture under cooling with ice/water. The obtained mixture was stirred for 30 minutes, followed by the addition of water. The mixture was acidified with concentrated hydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent. Thus, a brown oil was obtained. This oil was crystallized from isopropyl ether to obtain 1.0 g of the title compound as a light brown crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationconcentrated in a vacuum
  4. customto obtain a residue
  5. customto obtain a mixture
  6. customto obtain a solution
  7. additionThis solution was dropwise added to the above mixture
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. distillationdistilled
  11. customto remove the solvent
  12. customThus, a brown oil was obtained
  13. customThis oil was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3e3a8a9407384a2dad6761e0bac220ec
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

Loading…