Sodium Azide → HCID 178476915, compound

HRID 1763467Notes

Reaction equation

HRID 1763467 reaction equation
[CH2:1]([O:3][P:4]([O:12][CH2:13][CH3:14])([CH2:6][NH:7][C:8](=S)[S:9]C)=[O:5])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+]>C(O)C.O>[CH2:1]([O:3][P:4]([CH2:6][N:7]1[C:8]([SH:9])=[N:17][N:16]=[N:15]1)([O:12][CH2:13][CH3:14])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 20330789Diethyl ({[(methylsulfanyl)carbonothioyl]amino}methyl)phosphonate

Product 1

HCID 178476915HCID 178476915, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.85 g (11.1 mmol) of methyl 1-diethoxyphosphinylmethyldithiocarbamate in 25 ml of ethanol was added a solution of 0.72 g (11.1 mmol) of sodium azide in 5 ml of water. The reaction mixture was refluxed for 2.5 hours then evaporated to near dryness. Water (20 ml) was added and the aqueous mixture was layered with 40 ml of ethyl acetate and acidified to pH 2.2 by addition of 6N sulfuric acid. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The ethyl acetate solutions were combined, dried (MgSO4) and evaporated to dryness to give 1-diethoxyphosphinylmethyltetrazole-5-thiol.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. customthen evaporated
  3. additionWater (20 ml) was added
  4. additionacidified to pH 2.2 by addition of 6N sulfuric acid
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-17d64e06e30c4ee99ca37aa65b1a20b2
Source dataset
uspto-grants-1978_09
Patent number
US04112086

Reaction notes

Loading…