Thionyl Chloride → HCID 178443586, compound

HRID 275554Notes

Reaction equation

HRID 275554 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): δ1.3(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-56e40cd6b2bb4f93bac1245822a6e840
Source dataset
uspto-grants-1995_02
Patent number
US05393732

Reaction notes

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