Hydrogen Sulfide → p-Methoxybenzyl alpha-thioformamido-dimethylphosphonoacetate

HRID 1658029Notes

Reaction equation

HRID 1658029 reaction equation
[SH2:1].[NH2:2][CH:3]([P:16]([O:20][CH3:21])([O:18][CH3:19])=[O:17])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5].[CH:22]#N>CO>[CH:22]([NH:2][CH:3]([P:16]([O:20][CH3:21])([O:18][CH3:19])=[O:17])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[O:5])=[S:1]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 768Hydrogen CyanideHCID 21529965p-Methoxybenzyl alpha-amino-dimethylphosphonoacetate

Product 1

HCID 86733538p-Methoxybenzyl alpha-thioformamido-dimethylphosphonoacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen sulfide (0.75 g) is passed into a cold (ice-bath) solution of p-methoxybenzyl α-amino-dimethylphosphonoacetate (6.06 g) in anhydrous methanol (5 ml). Hydrogen cyanide (0.53 g) is added and the ice-bath is removed. After standing overnight, the reaction mixture is added to water (50 ml) and extracted with ether (3 × 20 ml). The combined extracts are dried with magnesium sulfate, filtered, and evaporated in vacuo to dryness. The residue is chromatographed on silicon gel, affording p-methoxybenzyl α-thioformamido-dimethylphosphonoacetate.

Workup

  1. customthe ice-bath is removed
  2. additionthe reaction mixture is added to water (50 ml)
  3. extractionextracted with ether (3 × 20 ml)
  4. dry with materialThe combined extracts are dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to dryness
  7. customThe residue is chromatographed on silicon gel

Sources & evidence

ORD record
ord-50bfde6056664fdaa664027ff73a64ed
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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