Sodium Carbonate → 2,2-Diethoxythioacetamide

HRID 1860392Notes

Reaction equation

HRID 1860392 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])([O-])=O.[Na+].[Na+].[CH2:21]([O:23][CH:24]([O:28][CH2:29][CH3:30])[C:25]([NH2:27])=O)[CH3:22]>C1COCC1.CC(=O)OCC>[CH2:21]([O:23][CH:24]([O:28][CH2:29][CH3:30])[C:25]([NH2:27])=[S:2])[CH3:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 1007652,2-Diethoxyacetamide

Product 1

HCID 27947342,2-DiethoxythioacetamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of phosphorus pentasulfide (27 g) in dry THF (100 ml) at 0° C. under vigorous stirring, Na2CO3 (13 g) was added. The reaction mixture was stirred for 30 min at 0° C. and for 30 min at r.t., then diethoxyacetamide (6 g) was added and stirring was continued at r.t. for 70 h. The reaction was then diluted with EA, washed with 10% Na3PO4, brine, dried over Na2SO4 and the solvent removed in vacuo. The crude residue was purified by flash-chromatography (EE/PE 1/1) to give the title compound as a white solid (4.4 g).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued at r.t. for 70 h
  4. washwashed with 10% Na3PO4, brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe crude residue was purified by flash-chromatography (EE/PE 1/1)

Sources & evidence

ORD record
ord-037d3a3fce9b483eb552b0c43bec90a2
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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