Imidazole → HCID 21339421, compound
Reaction equation
[S:1](Cl)(Cl)=[O:2].N1C=CN=C1.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][CH2:17][C@@H:18]([OH:21])[CH2:19][CH3:20]>ClCCl>[CH2:19]([C@@H:18]1[O:21][S:1](=[O:2])[N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)[CH2:17]1)[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Thionyl chloride (18.98 millimoles) in dichloromethane (20 ml) is added dropwise to imidazole (4.7 g, 69 millimoles) in dichloromethane (50 ml) under argon. Then after 15 minutes the title compound of part (a) (17.26 millimoles) in 25 ml of dichloromethane was added slowly at a temperature maintained below 5° C. After an hour at a temperature range of 0° to 5° the temperature was allowed to warm up to room temperature. After 1 hour, water was added The organic layer was separated and the aqueous layer was subjected to extraction with dichloromethane. The combined organic portions were washed twice with water, dried (sodium sulphate) and evaporated to give the title compound as an orange oil (3.325 g, 15.66 millimoles), NMR data δ(400 MHz; CDCl3) 1.11 (1.5 H, t,J 8 Hz), 1.12 (1.5 H, t,J 8 Hz), 1.88-2.05 (1.5 H, m), 2.11-2.22 (0.5 H, m), 3.32 (0.5 H, dd, J 10 and 8 Hz), 3.74 (0.5 H, dd, J 10 and 7 Hz), 3.93-4.02 (1 H, m) 4.84-4.91 (0.5 H, m), 5.35-5.42 (0.5 H, m), 6.63 (0.5 H, d, J 8 Hz), 6.73 (0.5 H, d, j 8 Hz), 6.88-6.94 (1 H, m), 7.59-7.65 (1 H, m) and 8.25-8.30 (1 H, m).
Sources & evidence
- ORD record
- ord-167c0ac9c0d0438f902ed09adf3149f2
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06133449
Reaction notes
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