Methanol → Sbb062309

HRID 1860463Notes

Reaction equation

HRID 1860463 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.N1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[OH:17]>>[C:12]([C:13]1[S:8][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:14]=1[CH3:15])(=[O:17])[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 737155Thionicotinamide

Product 1

HCID 1485005Sbb062309

Conditions

Temperature
72.5 °C

Procedure

A mixture of 5-chloro-pentadione (5.12 g, 38 mmol) and thionicotinamide (5.25 g, 38 mmol) in MeOH (10 mL) was treated with pyridine (3 mL). The reaction mixture was heated at 70-75° C. for 5 h. The solvent was evaporated. The resulting solid was filtered and washed with EtOAc/MeOH to afford 4.33 g 5-acetyl-4-methyl-2-(3-pyridyl)-thiazol as a yellow solid, which was subjected to the next reaction without further purification. A mixture of this material (2.0 g) and N,N-dimethylformamide dimethyl acetal (4 mL) was heated at 80° C. for 22 h. The reaction mixture was concentrated and then triturated with EtOAc/PE. The precipitates were collected and washed with EtOAc/PE to afford the title compound (2.05 g, 75%) as a grey solid. 1H-NMR (300 MHz, CDCl3) δ 2.80 (s, 6H, CH3), 3.50 (s, 3H, CH3), 5.47 (d, 1H, J=12.1 Hz, CH), 7.39 (m, 1H, Ar-H), 7.78 (d, 1H, J=12.1 Hz, CH), 8.28 (m, 1H, Ar-H), 8.66 (m, 1H, Ar-H), 9.16 (s, 1H, Ar-H).

Workup

  1. customThe solvent was evaporated
  2. filtrationThe resulting solid was filtered
  3. washwashed with EtOAc/MeOH

Sources & evidence

ORD record
ord-56ebd29531b44a018acaa4015d36d34f
Source dataset
uspto-grants-2003_03
Patent number
US06531479B2

Reaction notes

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