Thionyl Chloride → HCID 178443586, compound

HRID 582172Notes

Reaction equation

HRID 582172 reaction equation
S(Cl)([Cl:3])=O.[PH:5](=[O:8])([OH:7])[OH:6].[CH2:9]([C:11]([CH2:39][CH3:40])([CH:13](O)[C:14]1[N:18]=[CH:17][N:16]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]=1)[CH3:12])[CH3:10]>N1C=CC=CC=1>[PH:5](=[O:6])([OH:8])[OH:7].[CH2:9]([C:11]([CH2:39][CH3:40])([CH:13]([Cl:3])[C:14]1[N:18]=[CH:17][N:16]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]=1)[CH3:12])[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178444075HCID 178444075, compound

Product 1

HCID 178443586HCID 178443586, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (20 ml) was added dropwise to a stirred 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 pyridine (10 ml), whilst maintaining the temperature below 5° C. The mixture was allowed to warm to room temperature, stirred for three hours, then evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and brine, dried over magnesium sulphate and evaporated under reduced pressure. This residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3-chloro-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.64 g, m.p. 123-124° C.). NMR (CDCl3): δ 1.3(6H,t), 1.8-2.1(2H,m), 2.4-2.6(2H,m), 4.1(4H,m), 5.1(1H,t), 7.1(6H,m), 7.4(9H,m), 7.95(1H,s). M/S: M+ 523,525.

Workup

  1. temperaturewhilst maintaining the temperature below 5° C
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThis residue was chromatographed on silica

Sources & evidence

ORD record
ord-04d991e8703a4fa785547410b69282b8
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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