Compound 8m

3-(methylthio)-N,N'-di(thiazol-2-yl)propane-1,1-diamine

From: Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

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Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Prepared according to the general procedure outlined in 8. 1H NMR (600 MHz, DMSO-d6) δ 8.01 (d, J = 6.7 Hz, 2H, NH), 7.04 (d, J = 3.7 Hz, 2H, Ar), 6.65 (d, J = 3.7 Hz, 2H, Ar), 5.35 (br. qn, J = 7.0 Hz, 1H, (C1')–H), 2.55 (t, 2H, J = 7.0 Hz, (C3')–H2), 2.09 (q, J = 7.0 Hz, 2H, (C2')–H2), 2.05 (s, 3H, CH3,). 1H NMR (600 MHz, DMSO-d6 + D2O) δ 7.04 (d, J = 3.7 Hz, 2H, Ar), 6.65 (d, J = 3.7 Hz, 2H, Ar), 5.34 (t, J = 7.0 Hz, 1H, (C1')–H), 2.54 (t, J = 7.0 Hz, 2H, (C3')–H2), 2.08 (q, J = 7.0 Hz, 2H, (C2')–H2), 2.04 (s, 3H, CH3). 13C NMR (151 MHz, DMSO-d6) δ 167.6, 138.8, 107.0, 65.2, 33.9, 29.3, 14.8. HRMS ESI–TOF [M + H]+ cal. for C10H15N4S3 287.0459; obs. 287.0460. IR (solid, cm–1): 3203, 3143, 3070, 2960, 2916, 2879, 1597, 1556, 1498, 1460, 1448. M.p. 137–145 °C (decomp.). Single crystal X-ray structure (CCD 1477048; Supplementary Figure 161).

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