Pyridine → HCID 86669015, compound

HRID 2366281Notes

Reaction equation

HRID 2366281 reaction equation
[Br: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[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[C:7]=1F.NC(N)=[S:22].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Br: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[C:8]([Cl:12])=[N:9][CH:10]=[CH:11][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 86669016HCID 86669016, compound

Product 1

HCID 86669015HCID 86669015, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 2-bromo-6-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-benzimidoyl chloride (4.2 g, 11.0 mmol), thiourea (2.5 g, 33.0 mmol) and pyridine (3.1 mL, 38.4 mmol) in isopropanol (50 mL) under a nitrogen atmosphere was heated under reflux for 3 hours. Et3N (7.6 mL, 54.6 mmol) was added and the reaction mixture was heated under reflux for 1.5 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The resultant residue was triturated with water (100 mL) and then boiled in isopropanol (15 mL) for 10 minutes. After cooling to room temperature, the resultant solid was collected by filtration and then purified by column chromatography on silica gel eluting with 25% diethyl ether in pentane to afford the title compound as a colourless solid (2.1 g, 53%). LCMS (Method E): RT=4.16 min, m/z: 361 [M+H+].

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 1.5 hours
  4. customthe volatiles were removed under reduced pressure
  5. customThe resultant residue was triturated with water (100 mL)
  6. temperatureAfter cooling to room temperature
  7. filtrationthe resultant solid was collected by filtration
  8. custompurified by column chromatography on silica gel eluting with 25% diethyl ether in pentane

Sources & evidence

ORD record
ord-15e1b3dfc2784a45a0edc53a90442446
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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