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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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2023_BG_10A_1 - Thiourea formation on 2-amino-5-fluoropyridine #81

Closed KlementineJBS closed 11 months ago

KlementineJBS commented 1 year ago

Reaction scheme

image

Outcome

KlementineJBS commented 1 year ago
  1. Dissolved KSCN (942 mg, 9.6 mmol, 1.2 equiv.) in acetone (10 mL)
  2. Added benzoyl chloride (1 mL, 8.8 mmol, 1.1 equiv.)
  3. Stirred at 60 C for 50 minutes
  4. Added 2-amino-5-fluoropyridine (901 mg, 8 mmol)
  5. Stirred at 60 C for 1 hr

TLC indicated completion.

Work up as usual - see step 1.

Vial: 15.4202 full vial: 17.6727 Mass: 2.2525 g (8.18 mmol - over 100% yield)

KlementineJBS commented 1 year ago

LRMS

Peaks at 276.07 [M+H]+, 298.10 [M+Na]+, 572.99 [2M+Na]+, 274.02 [M-H]-, 571.11 [2M - 2H + Na]- all confirm presence of product.

2023_BG_10A_1.pdf 2023_BG_10A_100000.d.zip

KlementineJBS commented 1 year ago

H NMR

1H NMR (300 MHz, DMSO-d6) δ 13.26 (s, 1H), 11.80 (s, 1H), 8.75 (s, 1H), 8.49 (d, J = 3.0 Hz, 1H), 8.00 (d, J = 6 Hz, 2H), 7.90 (td, J = 8.6, 3.0 Hz, 1H), 7.70 (t, J = 9 Hz, 1H), 7.57 (t, J = 7.7 Hz, 2H).

2023_BG_10A_1_1.zip 2023_BG_10A_1.pdf

KlementineJBS commented 12 months ago

500 MHz NMR

1H NMR (500 MHz, DMSO-d6) δ 13.29 (s, 1H), 11.78 (s, 1H), 8.77 (s, 1H), 8.48 (d, J = 3.0 Hz, 1H), 8.03 – 7.96 (m, 2H), 7.94 – 7.86 (m, 1H), 7.73 – 7.65 (m, 1H), 7.60 – 7.48 (m, 2H).

19F NMR (471 MHz, DMSO) δ -130.05.

2023_BG_10A 500 MHz.pdf

230709_10A_1.zip 230709_10A_2.zip 230709_10A_3.zip