Triethylamine → 2-(Diethoxyphosphinyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1736320Notes

Reaction equation

HRID 1736320 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[NH:5][S:4]1(=[O:13])=[O:12].[P:14]([O-:22])([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[CH2:17]([O:16][P:14]([O:19][CH2:20][CH3:21])([O:22][CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[NH:5][S:4]1(=[O:13])=[O:12])=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5166299Diethyl phosphoric acidHCID 194244252-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194323452-(Diethoxyphosphinyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.42 mmol) was added to a solution of diethyl phosphate (Formula III: A=B=Et) (1.02 g; 6.62 mmol) in methylene chloride (5 ml) containing triethylamine (0.67 g; 6.63 mmol), and the mixture was allowed to reflux for 24 hours and then cooled. The mixture was concentrated in vacuo and the residue purified by silica gel flash chromatography (50% ethyl acetate/hexane) to afford 0.54 g (35%) of 2-(diethoxyphosphinyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2=propyl; R3 =H; A=B=Et) as an oil.

Workup

  1. temperatureto reflux for 24 hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue purified by silica gel flash chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f717ff31496446d9d785c262fd87a57
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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