Thionyl Chloride → HCID 178443552, compound
Reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:28]=[CH:27][C:17]([C:18]([NH:20][C@@H:21]([CH:24]([CH3:26])[CH3:25])[CH2:22][OH:23])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(Cl)(Cl)=O>C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]3[O:23][CH2:22][C@H:21]([CH:24]([CH3:25])[CH3:26])[N:20]=3)=[CH:27][CH:28]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 1.05 g of 4-(trans-4-heptylcyclohexyl)-N-[(S)-2-hydroxy-1-isopropylethyl)benzamide in 40 ml of acetenitrile was treated dropwise with 0.7 ml of thionyl chloride at 0° C. and while gassing with nitrogen. The reaction mixture was stirred at 0° C. overnight, poured into 100 ml of saturated potassium carbonate solution and then extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 50 ml of saturated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 2:1) and recrystallization from acetone at -25° C. gave pure (S)-2-[4-(trans-4-heptylcyclohexyl)phenyl]-4-isopropyl-2-oxazoline with m.p. (C-I) 51° C. and cl.p. (S-I) 46° C.