3-Pyridinecarboxaldehyde → HCID 9553196, compound

HRID 1911958Notes

Reaction equation

HRID 1911958 reaction equation
[C:1]1([NH:7][C:8](=[S:11])[NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>CO>[C:1]1([NH:7][C:8](=[S:11])[NH:9]/[N:10]=[CH:12]/[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 730679Hydrazinecarbothioamide, N-phenyl-

Product 1

HCID 9553196HCID 9553196, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

4-Phenylthiosemicarbazide (890 mg, 5.3 mmol, 1.0 equiv) was added to a stirred solution of nicotinaldehyde (500 μL, 5.3 mmol, 1.0 equiv) in methanol (2.5 mL) at 23° C. The resulting pale yellow solution was heated to 65° C. and stirred for 3 h. The cooled reaction mixture was concentrated under vacuum. The residue was rinsed with cold ethyl acetate and vacuum-filtered to afford the title compound as off-white crystals (1.3 g, 93%): mp 208-210° C.; IR (KBr thin film) 3442 (w), 3298 (m), 3125 (w), 2940 (w), 2791 (w), 1594 (s), 1532 (s) cm−1; 1H NMR (300 MHz, DMSO-d6) δ 11.98 (s, 1H), 10.22 (s, 1H), 9.03 (d, J=2 Hz, 1H), 8.59 (dd, J=5, 2 Hz, 1H), 8.38 (dt, J=8, 2 Hz, 1H), 8.18 (s, 1H), 7.55 (m, 2H), 7.45 (dd, J=8, 5 Hz, 1H), 7.21 (m, 1H); ESIMS m/z 257 ([M+H]+).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated under vacuum
  3. washThe residue was rinsed with cold ethyl acetate
  4. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-ca381df9af6842be911c9f0e1affe1f2
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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