1,2-Dichloroethane → HCID 66788634, compound
Reaction equation
O[CH2:2][C:3]1ON=C(C(OCC)=O)[CH:4]=1.C([N:16]([CH2:20][CH3:21])[CH:17]([CH3:19])C)(C)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+]([O-])=O)=[CH:28][CH:27]=1)=O.[Cl:35]CCCl>>[Cl:35][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH:23]2[CH2:4][C:3]3([CH2:19][CH2:17][NH:16][CH2:20][CH2:21]3)[CH2:2]2)=[CH:27][CH:28]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
0.172 g (1.00 mmole) of ethyl 5-hydroxymethyl-isoxazole-3-carboxylate and 0.33 ml (1.92 mmoles) of N,N-diisopropylethylamine are dissolved in 9 ml of 1,2-dichloroethane then cooled to 0° C. 0.184 g (0.91 mmole) of p-nitrophenyl chloroformate in solution in 2 ml of 1,2-dichloromethane are added. The mixture is stirred for 20 mins at ambient temperature, then 0.230 g (0.91 mmole) of 2-(4-chlorophenoxy)-7-aza-spiro[3.5]-nonane, obtained in stage 2.2, is added. The mixture is heated at 60° C. for 15 hrs. After return to ambient temperature, a 1N aqueous solution of caustic soda is added, and the product is extracted with dichloromethane. The combined organic phases are then successively washed three times with a 1N aqueous solution of caustic soda, twice with a saturated aqueous solution of ammonium chloride and once with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered and evaporated to dryness. 0.447 g of the expected product are obtained in the form of a colourless oil which is used as such in the following stage.
Sources & evidence
- ORD record
- ord-a76eb29cc0c7490e92b5554f28ba59c0
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394787B2
Reaction notes
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