Pyridine → HCID 3108186, compound

HRID 2243435Notes

Reaction equation

HRID 2243435 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1.N1C=CC=CC=1>ClCCCl.CN(C)C=O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[O:10])=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 183703-Methyl-4-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 3108186HCID 3108186, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-Nitro-3-methyl-benzoic acid (83 mmol) was suspended in 1,2-dichloroethane (500 mL) and dimethylformamide (DMF) (5 mL) under an argon atmosphere. Oxalylchloride (2M in dichloromethane, 62.3 mL) was added slowly to the stirred suspension. After stirring at room temperature for 1 h, the solvent was removed by evaporation under reduced pressure, and the reaction mixture was re-dissolved in 1,2-dichloroethane (400 mL). A suspension of 2-aminothiazole (83 mmol) and pyridine (83 mmol) in 1,2-dichloroethane (100 mL) was added portion wise. The reaction mixture was stirred at 50° C. over night. The solvent was removed under reduced pressure and the solids were re-suspended in ethyl acetate (500 mL) and NaHCO3 (sat.) (500 mL). The solids were removed by filtration and the liquid phases were separated. The organic phase was washed with NaHCO3 (sat.), dried over MgSO4, filtered and evaporated. The crude product was re-crystallized from ethyl acetate and the product fractions were combined to give 4-nitro-3-methyl-N-thiazol-2-yl-benzamide.

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. dissolutionthe reaction mixture was re-dissolved in 1,2-dichloroethane (400 mL)
  3. additionwas added portion wise
  4. stirringThe reaction mixture was stirred at 50° C. over night
  5. customThe solvent was removed under reduced pressure
  6. customThe solids were removed by filtration
  7. customthe liquid phases were separated
  8. washThe organic phase was washed with NaHCO3 (sat.)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe crude product was re-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d89bedf8aa334bc69e9043166105bb20
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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