Pyridine → HCID 66801575, compound

HRID 2366268Notes

Reaction equation

HRID 2366268 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[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:22].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]1[S:22][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 86669010HCID 86669010, compound

Product 1

HCID 66801575HCID 66801575, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-benzimidoyl chloride (15.4 g, 47.8 mmol), thiourea (14.5 g, 0.191 mol) and pyridine (19.3 mL, 0.239 mol) in isopropanol (250 mL) was heated at 85° C. for 4 hours under argon. To the mixture was added Et3N (40 mL, 0.287 mol) and heating at 85° C. was continued for 18 hours. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between EtOAc (500 mL) and water (500 mL). The aqueous phase was extracted with EtOAc (300 mL) and the combined organic layers were washed with water, then dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-50% EtOAc in pentane to afford the title compound as a pale yellow solid (8.5 g, 59%). LCMS (Method D): RT=3.56 min, m/z: 299 [M+H+].

Workup

  1. temperatureheating at 85° C.
  2. temperatureAfter cooling to room temperature
  3. customthe volatiles were removed under reduced pressure
  4. customthe resultant residue was partitioned between EtOAc (500 mL) and water (500 mL)
  5. extractionThe aqueous phase was extracted with EtOAc (300 mL)
  6. washthe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-50% EtOAc in pentane

Sources & evidence

ORD record
ord-0112f370230d47bdbbf3245159f4a8b6
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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