Hydrogen Sulfide → HCID 22066151, compound

HRID 1828321Notes

Reaction equation

HRID 1828321 reaction equation
[CH3:1][O:2][C:3](=O)[CH2:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)(Cl)Cl.[SH2:19]>>[CH3:1][O:2][C:3]1[S:19][C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][CH:4]=1

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 6212ChloroformHCID 14566Glycine, N-benzoyl-, methyl ester

Product 1

HCID 22066151HCID 22066151, compound

Conditions

Temperature
80 °C

Procedure

1.0 g (5.2 mmol) of benzoylglycin methyl ester and 1.4 g (6.4 mmol) of diphosphorous pentasulfide was added quickly into a reaction vessel. After that, anhydrous chloroform (15 ml) was also added and heated to around 80° C. When decrease in hydrogen sulfide generation and white precipitate formation in the reaction solution were observed, an argon balloon was attached and the solution was refluxed for 24 hours. After completion of reaction, the precipitate was dissolved by adding an aqueous solution of strong alkali to the solution, and the organic phase was extracted with dichloromethane, followed by drying with addition of magnesium sulfate and removal of solvent. The product was developed with ethyl acetate:hexane=5:5 solvent on a silica column to give 5-methoxy-2-phenylthiazole (Rf=0.40). The yield was 566 mg in weight and 57% in percentage.

Workup

  1. temperaturethe solution was refluxed for 24 hours
  2. customAfter completion of reaction
  3. dissolutionthe precipitate was dissolved
  4. additionby adding an aqueous solution of strong alkali to the solution
  5. extractionthe organic phase was extracted with dichloromethane
  6. dry with materialby drying with addition of magnesium sulfate and removal of solvent

Sources & evidence

ORD record
ord-fc3b09b721c949fa93cd050859934321
Source dataset
uspto-grants-2006_06
Patent number
US07057054B2

Reaction notes

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