Carbon Disulfide → HCID 10990345, compound

HRID 1297487Notes

Reaction equation

HRID 1297487 reaction equation
[H-].[Na+].[P:3]([O-:11])([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])=O.[H][H].[C:14](=[S:16])=[S:15].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.C(OCC)C>[CH2:9]([O:8][P:3]([C:14]([S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[S:15])([O:5][CH2:6][CH3:7])=[O:11])[CH3:10]

Participants

8

Reactant 5

HCID 6348Carbon DisulfideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 5166299Diethyl phosphoric acidHCID 178418361HCID 178418361, compound

Product 1

HCID 10990345HCID 10990345, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slur of sodium hydride (60% dispersion in mineral oil) (8 g, 0.2 mol) in tetrahydrofuran (200 mL) was added diethyl phosphate. (27.5 g, 0.2 mol) dropwise under nitrogen. The mixture was stirred until hydrogen evolution ceased (about 15 minutes). The mixture was allowed to cool in an ice-water bath and carbon disulfide (76 g, 1 mol) was added over 15 minutes followed by benzyl chloride (25.2 g, 0.2 mol) in THF (100 mL) over 20 minutes. The resultant mixture was stirred at room temperature for 24 hours. Diethyl ether (200 mL) was added and the mixture washed with water (3×200 mL). The organic layer was dried (MgSO4) filtered and evaporated in vacuo. After column chromatography (Kieselgel-60, 70-230 mesh, 1:4 ethyl acetate/n-hexane eluent), S-benzyl diethoxyphosphinyldithioformate (20) was obtained (11 g, 18% yield) as a red oil. 1H-nmr (CDCl3) d (ppm) 1.43 (t, 6H); 4.38 (s, 2H), 4.65 (q, 4H) and 7.30-7.45 (m, 5H).

Workup

  1. custom(about 15 minutes)
  2. temperatureto cool in an ice-water bath
  3. washthe mixture washed with water (3×200 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-836e41b9e5b14e4c8c5cc4a20bbb37be
Source dataset
uspto-grants-2007_07
Patent number
US07250479B2

Reaction notes

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