Chloroacetic Acid → Uracil-5-ylacetic acid

Reaction equation

[NH:1]1[CH:8]=[C:7]([CH2:9][C:10]([O:12]CC)=[O:11])[C:5](=[O:6])[NH:4][C:2]1=S.ClCC(O)=[O:18].Cl>O>[NH:1]1[CH:8]=[C:7]([CH2:9][C:10]([OH:12])=[O:11])[C:5](=[O:6])[NH:4][C:2]1=[O:18]

Participants

Procedure

Ethyl (2-thiouracil-5-yl)acetate (33, 7.8 g, 36 mmol) was mixed with chloroacetic acid (1.9 g, 20 mmol) and water (47 ml) and refluxed for 2 hours. Concentrated hydrochloric acid (22 ml) was added and the reaction mixture was refluxed overnight. The reaction mixture was filtered and the precipitate was washed once with water and dried. The procedure was repeated with the precipitate in place of 8 yielding 4.19 g (68%) of the title compound as a white solid. 1H-NMR (DMSO-d6/TMS): 2=3.13 (s, 2H, CH2COO); 7.35 (d, 1H, J=6.5 Hz, H-6); 10.74 (m, 1H, H-1); 11.09 (s, 1H, H-3); 12.20 (br, 1H, COOH). 13C-NMR (DMSO-d6/TMS): δ=31.3 (CH2COO); 106.6 (C-5); 139.7 (C-6); 151.2 (C-2); 164.0 (C-4); 171.9 (COOH).