Hydrazinecarboxaldehyde → HCID 178462183, compound

HRID 592264Notes

Reaction equation

HRID 592264 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([CH3:15])[C:12]([NH2:14])=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([NH:19][NH2:20])=O>C(O)C.[Hg](Cl)Cl>[N:19]1[N:20]=[C:12]([C@@H:11]([NH:10][C:9](=[O:16])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:15])[NH:14][CH:17]=1

Participants

5

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 15755199Phenylmethyl N-[(1S)-2-amino-1-methyl-2-thioxoethyl]carbamate

Product 1

HCID 178462183HCID 178462183, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl[(1S)-2-amino-1-methyl-2-thioxoethyl]carbamate (13.4 g, 56.2 mmol) in ethanol (1.125 L) was added formic acid hydrazide (20.26 g, 337 mmol) and mercury(II) chloride (19.85 g, 73.1 mmol). After 1 h the reaction was filtered and concentrated. Saturated aqueous sodium carbonate and ethyl acetate were added. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. A solution of the resulting residue in ethanol (1.125 L) was heated to 80° C. After 16 h, the reaction was concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol with 1% ammonium hydroxide) gave the title compound (8.7 g). MS 247.1 (M+1).

Workup

  1. filtrationAfter 1 h the reaction was filtered
  2. concentrationconcentrated
  3. additionSaturated aqueous sodium carbonate and ethyl acetate were added
  4. customThe organic layer was isolated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. concentrationthe reaction was concentrated
  11. customPurification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol with 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-066512c2e1df4220833a6921678431d6
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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