Trityl chloride → HCID 10717786, compound
Reaction equation
[CH2:1]([O:3][C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[N:14]=[CH:13][NH:12][N:11]=2)[O:6][N:5]=1)[CH3:2].C(N(CC)CC)C.[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:1]([O:3][C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[N:14]=[CH:13][N:12]([C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:11]=2)[O:6][N:5]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(3-Ethoxy-4-methylisoxazol-5-yl)-1H-1,2,4-triazole (1.1 g, 5.7 mmol), triethylamine (2.5 mL, 18 mmol) and DMF (20 mL) was added trityl chloride (1.6 g, 5.7 mmol) in DMF (5 mL). The mixture was stirred at room temperature for 5 h and poured onto an ice/water mixture (200 mL). The aqueous phase was extracted with diethyl ether (3×200 mL) and the organic extracts were washed with an aqueous solution of Na2CO3 (10%) (200 mL) and brine (200 mL). The solution was dried (Na2SO4) and concentrated in vacuo to give crude title compound (2.5 g). A small sample was crystallized (EtOAc) to give a single isomer as colourless crystals: mp 181-183° C. The crude product was used in the next step without further purification.
Workup
- extractionThe aqueous phase was extracted with diethyl ether (3×200 mL)
- washthe organic extracts were washed with an aqueous solution of Na2CO3 (10%) (200 mL) and brine (200 mL)
- dry with materialThe solution was dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-545c402417134d8a9fbfdd9935256604
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06200999B1
Reaction notes
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