(Diethylamino)sulfur trifluoride → HCID 178443894, compound

HRID 582171Notes

Reaction equation

HRID 582171 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[CH2:5]([C:7]([CH2:35][CH3:36])([CH:9](O)[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6].C(N(S(F)(F)[F:43])CC)C>ClCCl>[PH:1](=[O:2])([OH:4])[OH:3].[CH2:5]([C:7]([CH2:35][CH3:36])([CH:9]([F:43])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 178444075HCID 178444075, compound

Product 1

HCID 178443894HCID 178443894, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of diethyl 3-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 24) in dichloromethane (3 ml) was added dropwise with stirring at -70° C., to a solution of diethylaminosulphur trifluoride (0.37 g) in dichloromethane (7 ml). The mixture was stirred at -70° C. for two hours, allowed to warm to room temperature and, after a further one hour, diluted with dichloromethane, washed with water and sodium bicarbonate solution, dried over magnesium sulphate, and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (19:1) as eluant, to give diethyl 3-fluoro-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.50 g, m.p. 97-98° C.). NMR (CDCl3): δ 1.3(6H,t), 1.7-2.0(2H,m), 2.1-2.5(2H,m), 4.1(4H,m), 5.5-5.7(1H,m), 7.1-7.3(15H,m), 7.95(1H,s). M/S: M+ 507.

Workup

  1. temperatureto warm to room temperature and, after a further one hour
  2. washwashed with water and sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-471bf8c003b74c1b9c87a84b72eecadf
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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