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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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KBS31-1 - Thiourea formation on 2-amino-5-methylpyridine fragment #109

Closed KlementineJBS closed 1 year ago

KlementineJBS commented 1 year ago

Reaction scheme

KBS31 and KBS32

Outcome

955 mg, 76%

KlementineJBS commented 1 year ago

30.06.23

  1. Added KSCN (542 mg, 5.58 mmol, 1.2 equiv.)

  2. Added benzoyl chloride (0.6 mL, 714 mg, 5.08 mmol, 1.1 equiv.)

  3. Dissolved in acetone (10 mL)

  4. Stirred at 65 C for 30 minutes

  5. Added 2-amino-5-methylpyridine (500 mg, 4.62 mmol)

  6. Stirred at 65 C for 20 minutes. Turned off over the weekend and stirred for 45 minutes at 65 C on Monday morning.

  7. TLC indicated formation of product.

  8. Cooled in an ice bath and vacuum filtered.

  9. Washed with cold water and isopropanol - IPA appeared to efficiently remove a yellow impurity.

Vial: 15.5191 Full vial: 16.4742 Mass: 955.1 mg (3.52 mmol, 76%).

Note that a fair amount of yellow crystalline powder was present in filtrate - this probably represents missing 24%.

KlementineJBS commented 1 year ago

NMR

1H NMR (300 MHz, DMSO-d6) δ 13.23 (s, 1H), 11.68 (s, 1H), 8.66 (s, 1H), 8.33 – 8.26 (m, 1H), 8.04 – 7.95 (m, 2H), 7.80 – 7.64 (m, 2H), 7.59 (d, J = 7.8 Hz, 2H), 2.32 (s, 3H).

KBS31-1.pdf KBS31-1_1.zip

KlementineJBS commented 1 year ago

LRMS

Peaks at 272.16 [M+H]+, 294.10 [M+Na]+, 565.09 [2M+Na]+, 270.09 [M-H]-, 563.15 [2M - 2H + Na]- confirm product.

KBS31-1.d.zip KBS31-1.pdf