Thionyl Chloride → HCID 18466605, compound

HRID 2229338Notes

Reaction equation

HRID 2229338 reaction equation
C([O-])(O)=O.[Na+].N[C:7]1[C:8]([Cl:14])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1.[Br:15][C:16]1[CH:17]=[C:18]([C:23](Cl)=[O:24])[C:19]([Cl:22])=[N:20][CH:21]=1.BrC1C=C(C(O)=O)C(O)=[N:31]C=1.O=S(Cl)Cl>CC#N.O>[Br:15][C:16]1[CH:17]=[C:18]([C:23]([NH:31][C:11]2[C:10]([CH3:13])=[N:9][C:8]([Cl:14])=[CH:7][CH:12]=2)=[O:24])[C:19]([Cl:22])=[N:20][CH:21]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27344153-Amino-2-chloro-6-picolineHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chlorideHCID 178418525HCID 178418525, compound

Product 1

HCID 18466605HCID 18466605, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

NaHCO3 (3.9 g, 46.4 mmol) was added to a solution of 3-amino-2-chloro-6- methylpyridine (2.2 g, 15.4 mmol; prepared as described by K. G. Grozinger et al. J. Heterocyclic Chem. 1995,32,259-263) in MeCN (50 mL). The resulting suspension was stirred for 15 min. and a solution of crude 5-bromo-2-chloro-3-pyridinecarbonyl chloride (prepared from 5-bromo-2-hydroxy-3-pyridinecarboxylic acid and SOCl2 [as described by T. W. Gero et al. in Synth. Commun. 1989, 19, 553-559 (incorporated herein by reference) but with omission of the aqueous work-up] (4 g,) in MeCN (10 mL) was introduced over 30 min. The resulting suspension was stirred at room temperature. After 24 h, the mixture was poured into a mixture of water (100 mL) and ice (10 g) and stirred for 20 min. The suspension was filtered and the resulting solid was washed with water (50 mL) and hexane (25 mL), then dried over P2O5 under reduced pressure to give the title compound (1.8 g, 31% yield) as a white powder.

Workup

  1. additionwas introduced over 30 min
  2. stirringThe resulting suspension was stirred at room temperature
  3. waitAfter 24 h
  4. stirringstirred for 20 min
  5. filtrationThe suspension was filtered
  6. washthe resulting solid was washed with water (50 mL) and hexane (25 mL)
  7. dry with materialdried over P2O5 under reduced pressure

Sources & evidence

ORD record
ord-64ffff2fae2446a8ab771d7dbb27aa46
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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