Water → HCID 70011121, compound

HRID 1368026Notes

Reaction equation

HRID 1368026 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=[N:13]1.[B-](Br)(Br)(Br)[S+](C)C.O>ClC(Cl)C>[CH2:14]([C:9]1[O:8][C:7]2[C:6]([Cl:10])=[CH:5][C:4]([F:11])=[C:3]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=[N:13]3)[C:2]=2[N:1]=1)[CH:15]([CH3:19])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4181510Tribromoborane-methyl sulfideHCID 18519609HCID 18519609, compound

Product 1

HCID 70011121HCID 70011121, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 2-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one (0.39 g) and borontribromide-methyl sulfide complex (1.8 g) in dichloroethane was heated at reflux temperature for 1 hour under nitrogen atmosphere. The mixture was poured into water and extracted with methylene dichloride. The organic phase was dried over anhydrous sodium sulfate and concentrated to give the title compound. 1H NMR (CDCl3, 300 MHz) 4.61 (3H, br s), 6.55 (1H, d, J=9.4 Hz), 7.30 (1H, m), 8.05 (1H, d, J=2.2 Hz) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour under nitrogen atmosphere
  3. extractionextracted with methylene dichloride
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-539f47259ebd44acb5712e483c25537b
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

Loading…