Carbon Dioxide → HCID 86733537, compound

HRID 1658023Notes

Reaction equation

HRID 1658023 reaction equation
[NH2:1][CH:2]([P:16]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:4].[SH2:32].[C:33](=O)=O>>[CH:33]([NH:1][CH:2]([P:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:17])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:4])=[S:32]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 402Hydrogen SulfideHCID 54227761HCID 54227761, compound

Product 1

HCID 86733537HCID 86733537, compound

Procedure

A mixture of p-nitrobenzyl α-amino-diphenylphosphonoacetate (5.0 g), ethyl thionoformate (5 ml), and hydrogen sulfide (5 ml) in a sealed thick-walled tube is left standing overnight at room temperature. The tube is cooled in dry-ice and the seal removed. A boiling chip is placed in the solution and it is allowed to slowly come to room temperature. Nitrogen is bubbled in to remove final traces of hydrogen sulfide. The residue is dissolved in methylene chloride, filtered, and evaporated under reduced pressure. Chromatography of the residue on silica gel gives p-nitrobenzyl α-thioformamido-diphenylphosphonoacetate.

Workup

  1. waitis left
  2. customthe seal removed
  3. customto slowly come to room temperature
  4. customNitrogen is bubbled in
  5. customto remove final traces of hydrogen sulfide
  6. dissolutionThe residue is dissolved in methylene chloride
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f8ac047c48f84f53b81405a18b76f723
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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