Sodium Sulfide → HCID 131721058, compound

HRID 341786Notes

Reaction equation

HRID 341786 reaction equation
F[B-](F)(F)F.N#[O+].[CH2:8]([O:10][P:11]([CH:16]([NH:25][C:26]1[CH:31]=[CH:30][C:29](N)=[CH:28][N:27]=1)[P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9].[S-2:33].[Na+].[Na+]>C(Cl)Cl>[CH2:8]([O:10][P:11]([CH:16]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([SH:33])=[CH:28][N:27]=1)[P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 11137142Nitrilooxonium tetrafluoroborateHCID 54067045HCID 54067045, compound

Product 1

HCID 131721058HCID 131721058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To nitrosonium tetrafluoroborate (NOBF4) (22 mg, 0.19 mmol) in methylene chloride (6 ml) at room temperature is added [(5-amino-2-pyridinyl)aminomethylene]bis[phosphonic acid] tetraethyl ester (75 mg, 0.19 mmol). The reaction mixture is stirred 3 hours then concentrated under reduced pressure. The crude residue is dissolved in acetonitrile (6 ml) and sodium sulfide (46 mg, 0.19 mmol) is added. After stirring 12 hours at room temperature, the reaction is quenched by the addition of water and the mixture is extracted with methylene chloride. The organic extracts are combined and washed with 10% aqueous Na2S2O3. The organic extracts are then dried over sodium sulfate, filtered and concentrated under reduced pressure. The desired thiol is obtained by flash chromatography purification with 2% isopropanol in methylene chloride.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe crude residue is dissolved in acetonitrile (6 ml)
  3. stirringAfter stirring 12 hours at room temperature
  4. customthe reaction is quenched by the addition of water
  5. extractionthe mixture is extracted with methylene chloride
  6. washwashed with 10% aqueous Na2S2O3
  7. dry with materialThe organic extracts are then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7431d6e7465548e48f46d4bc045c7308
Source dataset
uspto-grants-1999_01
Patent number
US05856314

Reaction notes

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