Triethylamine → HCID 19432346, compound

HRID 1736314Notes

Reaction equation

HRID 1736314 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH:9]([CH3:11])[CH3:10])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13].[P:15]([O-:23])([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH2:18]([O:17][P:15]([O:20][CH2:21][CH3:22])([O:23][CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH:9]([CH3:11])[CH3:10])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5166299Diethyl phosphoric acidHCID 19424418HCID 19424418, compound

Product 1

HCID 19432346HCID 19432346, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloromethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g) was added to a solution of diethyl phosphate (Formula III: A=B=Et) (0.48 g) in methylene chloride containing triethylamine (0.31 g), and the mixture was allowed to reflux for 48 hours and then cooled. The mixture was concentrated in vacuo and the residue purified by silica gel flash chromatography (ethyl acetate/hexane) to afford 0.36 g (48%) of 2-(diethoxyphosphinyloxymethyl)-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2 =isopropyl; R3 =CH3 ; A=B=Et) as an oil.

Workup

  1. temperatureto reflux for 48 hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue purified by silica gel flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c7810e7a37a44dc2899d5e62e0f48f73
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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