3-Chlorobenzaldehyde → HCID 74762711, compound

Participants

Reaction Steps

4-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3-chlorobenzaldehyde (182 mg, 147 μl, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 Eq: 0.3) were dissolved in MeOH (2.00 mL). The resulting colorless solution was stirred at rt. To this solution was added dropwise 2-isocyano-2-methylpropane (103 mg, 140 μL, 1.23 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. To the yellow clear solution was added dropwise water until the mixture got turbid and the product precipitated from the MeOH/water mixture. The solid was filtered off, washed with MeOH/water (1:1) and hexane and dried under vacuum, to give a yellow solid (238 mg, 52.5%). MS: 367.0 [M]+; 1H-NMR (D6-DMSO): δ 8.63 (d, 1H), 8.29 (s, 1H), 8.18 (d, 1H), 8.00 (s, 1H), 7.49 (t, 1H), 7.40 (d, 1H), 7.15 (d, 1H), 4.95 (s, 1H), 1.04 (s, 9H).

Provenance & Evidence