2023_BG_8A_1 - Thiourea formation on 2-amino-5-methoxypyridine

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Reaction scheme

Outcome

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1. Dissolved KSCN (941 mg, 9.6 mmol) in acetone (30 mL)
2. Added benzoyl chloride (1 mL, 8.8 mmol)
3. Stirred at 60 C for 2 hrs
4. Added aniline (987 mg, 8 mmol)
5. Stirred at 60 C for 1 hr

TLC indicated completion.

Work up as usual - see step 1.

Vial: 15.4378 Full vial: 17.6088 Mass: 2.171 g (7.56 mmol, 94%)

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H NMR

1H NMR (300 MHz, DMSO) δ 13.18 (s, 1H), 11.66 (s, 1H), 8.64 (d, J = 9.1 Hz, 1H), 8.18 (d, J = 3.0 Hz, 1H), 8.00 (dt, J = 7.1, 1.3 Hz, 2H), 7.74 – 7.65 (t, 1H), 7.62 – 7.50 (m, 3H), 3.88 (s, 3H).

2023_BG_8A_1_1.zip 2023_BG_8A_1.pdf

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LRMS

Peak at 310.10 [M+Na]+ confirms product is present.

2023_BG_8A.d.zip 2023_BG_8A_1.pdf

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500 MHz NMR

1H NMR (500 MHz, DMSO-d6) δ 13.18 (s, 1H), 11.65 (s, 1H), 8.65 (d, J = 8.8 Hz, 1H), 8.18 (d, J = 3.0 Hz, 1H), 8.03 – 7.96 (m, 2H), 7.72 – 7.65 (m, 1H), 7.63 – 7.51 (m, 3H), 3.87 (s, 3H).

13C NMR (126 MHz, DMSO) δ 177.37, 168.64, 153.55, 144.16, 135.38, 133.16, 132.07, 128.73, 128.41, 128.16, 127.43, 122.27, 117.00, 55.92.

230709_BG8A_1 (2).zip 230709_BG8A_2 (1).zip 2023_BG_8A 500 MHz.pdf