Hydrogen Sulfide → HCID 19775537, compound

HRID 1613242Notes

Reaction equation

HRID 1613242 reaction equation
[SH2:1].C([CH2:4][C:5]([O:7][CH3:8])=[O:6])#N.[N:9]1C=CC=[CH:11][CH:10]=1.C(N(CC)CC)C>>[C:10]([NH:9][CH2:4][C:5]([O:7][CH3:8])=[O:6])(=[S:1])[CH3:11]

Participants

5

Reactant 4

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 7747Methyl cyanoacetateHCID 8471Triethylamine

Product 1

HCID 19775537HCID 19775537, compound

Procedure

A stream of H2S is bubbled into a mixture of methyl cyanoacetate (70 g, 710 mmol), pyridine (70 ml, 710 mmol) and triethylamine (49.6 ml, 350 mmol). The exothermic reaction, which is cooled with an ice bath, is followed by TLC. When the reaction is complete, the reaction mixture is washed with a dilute solution of acid and extracted with ether. After drying over magnesium sulfate and concentration under vacuum, an orange oil is obtained which crystallizes. The yellow solid obtained is washed with ether and then filtered off to give 83.3 g of methyl thioacetamidoacetate melting at 78°-9° C.

Workup

  1. customThe exothermic reaction, which
  2. temperatureis cooled with an ice bath
  3. washthe reaction mixture is washed with a dilute solution of acid
  4. extractionextracted with ether
  5. dry with materialAfter drying over magnesium sulfate and concentration under vacuum
  6. customan orange oil is obtained which
  7. customcrystallizes
  8. customThe yellow solid obtained
  9. washis washed with ether
  10. filtrationfiltered off

Sources & evidence

ORD record
ord-4f7df15a3c0a47ac9a569e2daf649db7
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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