Pyridine → HCID 66801667, compound

HRID 2366290Notes

Reaction equation

HRID 2366290 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](Cl)=[N:5][C:6]1[C:11]([F:12])=[CH:10][N:9]=[CH:8][C:7]=1F.NC(N)=[S:24].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]1[S:24][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([F:12])[C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 86669019HCID 86669019, compound

Product 1

HCID 66801667HCID 66801667, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 2-chloro-N-(3,5-difluoropyridin-4-yl)-6-nitrobenzimidoyl chloride (5.53 g, 16.6 mmol), thiourea (5.05 g, 0.066 mol) and pyridine (6.7 mL, 83 mmol) in isopropanol (90 mL), under nitrogen, was heated under reflux for 6 hours. After this time, Et3N (14 mL, 100 mmol) was added over 5 minutes and the reaction mixture was heated under reflux for 18 hours. Upon cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were dried (Na2SO4) and concentrated to dryness. The resultant residue was purified by column chromatography on silica gel eluting with 0-80% EtOAc in pentane followed by 0-50% EtOAc in DCM to afford the title compound as a yellow solid (2.55 g, 50% yield). LCMS (Method D): RT=3.29 min, m/z: 310 [M+H+].

Workup

  1. temperatureunder nitrogen, was heated
  2. temperatureunder reflux for 6 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 18 hours
  5. customthe volatiles were removed under reduced pressure
  6. customthe resultant residue was partitioned between water and EtOAc
  7. extractionThe aqueous phase was further extracted with EtOAc (×2)
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. concentrationconcentrated to dryness
  10. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-80% EtOAc in pentane

Sources & evidence

ORD record
ord-334b6985921543189852a08046e98dd9
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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