2,6-Dichloro-isonicotinoyl chloride → 6-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469317Notes

Reaction equation

HRID 469317 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][C:13]1[C:18]2[NH:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.[Cl-].[Cl-].[Cl-].[Al+3]>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:15]2[CH:14]=[C:13]([CH3:12])[C:18]3[NH:19][C:20](=[O:22])[O:21][C:17]=3[CH:16]=2)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 27816432,6-Dichloro-isonicotinoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

Product 1

HCID 581812126-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.00 g (14.3 mmol) 2,6-dichloropyridine-4-carboxylic acid chloride, 1.80 g (11.0 mmol) 4-methyl-3H-benzoxazol-2-one and 9.47 g (71.0 mmol) aluminium trichloride were combined and heated for 2 h to 125° C. with stirring. Then the mixture was decomposed with ice water and EtOAc and the phases were separated. The aqueous phase was extracted several times with EtOAc. The organic phases were combined, dried on sodium sulphate, filtered and the filtrate was evaporated down i. vac. The residue was triturated with diethyl ether, the precipitate was suction filtered and dried i. vac.

Workup

  1. temperatureheated for 2 h to 125° C.
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted several times with EtOAc
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customthe filtrate was evaporated down i
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered
  9. customdried i

Sources & evidence

ORD record
ord-d8a2718c0911453f9d47a4de7cf71a7f
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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