Water → HCID 178444211, compound

HRID 582180Notes

Reaction equation

HRID 582180 reaction equation
[CH3:1][S-:2].[Na+].[PH:4](=[O:7])([OH:6])[OH:5].[CH2:8]([C:10]([CH2:38][CH3:39])([CH:12](I)[C:13]1[N:17]=[CH:16][N:15]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1)[CH3:11])[CH3:9].O>C(O)C>[PH:4](=[O:5])([OH:7])[OH:6].[CH2:8]([C:10]([CH2:38][CH3:39])([CH:12]([S:2][CH3:1])[C:13]1[N:17]=[CH:16][N:15]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1)[CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 178443937HCID 178443937, compound

Product 1

HCID 178444211HCID 178444211, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium thiomethoxide (0.24 g) was added to a stirred solution of diethyl 3-iodo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 30) in ethanol (10 ml). The mixture was stirred for five hours, allowed to stand overnight, poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3-methylthio-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.60 g, m.p. 97-98° C.). NMR (CDCl3): δ 1.3(6H,dt), 1.7-1.9(2H,m), 1.9(3H,s), 2.2-2.4(2H,m), 3.9(1H,t), 4.05(4H,m), 7.1(6H,m), 7.3(9H,m), 7.9(1H,s). FAB M/S: MH+ 536.

Workup

  1. waitto stand overnight
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-8d5fa0ee77fe433cab5b071a57f9710e
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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