Table 1. Reaction of N-phenylthiourea with methyl 4-bromocrotonate a .
| ||
S. no. | Solvent | Yield (%) |
1 | HFIP | 90 |
2 | 2,2,2-Trifluroethanol | 74 |
3 | CH2Cl2 | 50 |
4 | CHCl3 | 55 |
5 | CH3OH | 60 |
6 | CH3CH2OH | 50 |
7 | Isopropanol | 65 |
8 | 1-Propanol | 55 |
9 | 2-Butanol | 60 |
10 | CH3CN | 48 |
11 | THF | 40 |
12 | Acetone | NR |
13 | DMF | NR |
14 | DMSO | NR |
15 | H2O | NR |
16 | Neat | NR |
17 | HFIP : MeOH (1 : 1) | 64 |
aReaction conditions: substrate (1.0 mmol), Michael acceptor (1.1 mmol), sodium acetate (1.1 mmol), and HFIP solvent (5 mL).