Phosphorus oxychloride → HCID 86707952, compound
Reaction equation
O[C:2]1[C:3]2[C:4]3[CH:5]=[C:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[CH:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1[C:3]2[C:4]3[CH:5]=[C:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[CH:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1Participants
Procedure
A solution of ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5,10,12-hexaen-12-yl]acetate (2.10 g, 7.28 mmol, 1.00 equiv) in POCl3 (23 mL) was stirred for 1 h at 90° C. in an oil bath. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue dissolved in EtOAc was poured into a cooled saturated aqueous sodium bicarbonate, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1:5) to afford ethyl 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5,10,12-hexaen-12-yl]acetate (1.61 g, 72%) as a white solid. LCMS (ES, m/z): 307 and 309 (M+H+).
Workup
- concentrationconcentrated under reduced pressure
- dissolutionThe residue dissolved in EtOAc
- additionwas poured into a cooled saturated aqueous sodium bicarbonate
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1:5)
Sources & evidence
- ORD record
- ord-6a3750ef82444c65bac794587987b169
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085586B2
Reaction notes
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