Pyridine → HCID 86669017, compound

HRID 2366287Notes

Reaction equation

HRID 2366287 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1F)=O.NC(N)=[S:24].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:13][C:9]1[C:8]2[S:24][C:4]([C:3]3[C:15]([N+:19]([O-:21])=[O:20])=[CH:16][CH:17]=[CH:18][C:2]=3[Cl:1])=[N:6][C:7]=2[CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 86669018HCID 86669018, compound

Product 1

HCID 86669017HCID 86669017, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred suspension of 2-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-6-nitrobenzamide (3.90 g, 11.2 mmol), thiourea (3.40 g, 44.8 mmol) and pyridine (3.1 mL, 38.1 mmol) in isopropanol (35 mL) under a nitrogen atmosphere, was heated under reflux for 4 hours. After this time, Et3N (9.4 mL, 67.2 mmol) was added and the reaction mixture was heated under reflux for 16 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The crude residue was triturated with ethyl acetate and the solid was removed by filtration. The resultant filtrate was washed with 10% citric acid, brine, dried over MgSO4 and evaporated under reduced pressure to afford the title compound as a pale orange solid (3.55 g, 97%). 1H NMR (400 MHz, CDCl3): δ 8.51 (d, J=5.5 Hz, 1H), 8.13 (dd, J=1.2, 8.4 Hz, 1H), 7.91 (d, J=5.7 Hz, 1H), 7.87 (dd, J=1.2, 8.3 Hz, 1H), 7.72 (t, J=8.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 16 hours
  5. customthe volatiles were removed under reduced pressure
  6. customThe crude residue was triturated with ethyl acetate
  7. customthe solid was removed by filtration
  8. washThe resultant filtrate was washed with 10% citric acid, brine
  9. dry with materialdried over MgSO4
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-442ab740c5c24e6ab890c4c667a5149b
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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