Pyridine → HCID 85951409, compound

HRID 2110953Notes

Reaction equation

HRID 2110953 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.C(Cl)Cl.[C:19](Cl)(Cl)=[S:20].N1C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]=[C:19]=[S:20])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 10040Thiophosgene2×HCID 28412179HCID 28412179, compound

Product 1

HCID 85951409HCID 85951409, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3-Fluorophenoxy)-2-pyridinamine (210 mg, 1 mmol) was dissolved in dry degassed methylene chloride (5 ml) and thiophosgene (0.11 ml, 1.3 mmol) was added through syringe during 5-10 min to the stirred solution. Pyridine (0.18 ml, 2 mmol) was added to the reaction mixture right after the addition of thiophosgene and the reaction mixture was stirred at ambient temperature for 1.5-2 h. Then the reaction mixture was poured into water (15 ml) and extracted into methylene chloride (3×20 ml). Organic extract was washed with water and brine and dried over magnesium sulfate. Solvent was then removed by rotary evaporation and the oil obtained was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3) to give 190 mg of pure product as dark brown-purple solid. Yield 75%.

Workup

  1. customin dry
  2. additionwas added through syringe during 5-10 min to the stirred solution
  3. extractionextracted into methylene chloride (3×20 ml)
  4. extractionOrganic extract
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customSolvent was then removed by rotary evaporation
  8. customthe oil obtained
  9. customwas purified by column chromatography on silica (30 g, EtOAc/hexane 1:3)

Sources & evidence

ORD record
ord-e34ecffc335d410c99c7e77bd21657fc
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

Loading…