Hydrogen Sulfide → Thioformamido-diethylphosphonoacetic acid tert.-butyl ester

HRID 1390254Notes

Reaction equation

HRID 1390254 reaction equation
[SH2:1].[C:2]([O:6][C:7](=[O:19])[CH:8]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])[N+:9]#[C-:10])([CH3:5])([CH3:4])[CH3:3]>O1CCCC1.[Cu]>[C:2]([O:6][C:7](=[O:19])[CH:8]([NH:9][CH:10]=[S:1])[P:11]([O:13][CH2:14][CH3:15])([O:16][CH2:17][CH3:18])=[O:12])([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 57315705HCID 57315705, compound

Product 1

HCID 86735044Thioformamido-diethylphosphonoacetic acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dry hydrogen sulphide gas is passed for 10 minutes into a solution, cooled to 0° C., of 277 mg (1 mmol) of diethylphosphono-isocyanoacetic acid tert.-butyl ester in 5 ml of dry tetrahydrofurane (filtered through aluminium oxide). After adding a few crystals of copper-II acetylacetonate, the reaction vessel is closed and left to stand overnight at room temperature. The reaction mixture is filtered and the filtrate is evaporated in vacuo. The residue is chromatographed on silica gel thick layer plates with toluene/ethyl acetate, 1:1, and gives thioformamido-diethylphosphonoacetic acid tert.-butyl ester in the form of a colourless oil: IR spectrum (in methylene chloride): characteristic bands at 3.13; 3.35; 5.75; 7.01; 8.10; 8.70 and 9.75μ.

Workup

  1. customthe reaction vessel is closed
  2. waitleft
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated in vacuo
  5. customThe residue is chromatographed on silica gel thick layer plates with toluene/ethyl acetate, 1:1

Sources & evidence

ORD record
ord-05312055744e400686e8a7747af98f01
Source dataset
uspto-grants-1979_02
Patent number
US04138451

Reaction notes

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