3,3-Dimethylbutanoyl chloride → HCID 24871517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-fluoro-benzyloxy)-benzene-1,2-diamine (0.23 g, 1 mmol) and N,N-diisopropylethyllamine (0.21 ml, 1.2 mmol) in 8 ml of anhydrous ethanol was added dropwise tert-butylacetylchloride (111 μl, 1 mmol) at 4-5° C. in an ice-water bath. The reaction mixture was stirred for 30 min at 4-5° C. and for 3 hours at room temperature. The solvent was removed in vacuo and the residue was chromatographied (hexane/ethyl acetate, 2:1) to give the desired product as a white solid. 1H-NMR (300 MHz, DMSO-d6): δ 8.94 (brs, 1H, exchangeable with D2O, NH), 7.44 (dd, J=5.7 and 8.7 Hz, 2H), 7.18 (t, J=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 1H), 6.34 (d, J=2.7 Hz, 1H), 6.18 (dd, J=8.7 and 2.7 Hz, 1H), 4.95 (s, 2H), 4.79 (brs, 2H, exchangeable with D2O, NH2), 2.13 (s, 2H), 1.00 (s, 9H). MS: 331 (M+1).

Provenance & Evidence