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

HRID 469328Notes

Reaction equation

HRID 469328 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]>>[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

4

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

Procedure

10.0 g (47.5 mmol) 2,6-dichloropyridine-4-carboxylic acid chloride, 7.08 g (47.5 mmol) 4-methyl-3H-benzoxazol-2-one and 32.0 g (240 mmol) aluminium trichloride were heated to 120° C. for 1 h with stirring. The mixture was mixed with ice water and extracted several times with EtOAc. The solid precipitated from EtOAc was suction filtered and washed with EtOAc. The organic phase remaining was separated off, dried on sodium sulphate, filtered and evaporated down. The residue was combined with a little EtOAc, the precipitated solid was suction filtered and washed with a little EtOAc. For further purification the mixture was recrystallised from EtOAc.

Workup

  1. extractionextracted several times with EtOAc
  2. customThe solid precipitated from EtOAc
  3. filtrationfiltered
  4. washwashed with EtOAc
  5. customThe organic phase remaining was separated off
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down
  9. filtrationfiltered
  10. washwashed with a little EtOAc
  11. customFor further purification the mixture
  12. customwas recrystallised from EtOAc

Sources & evidence

ORD record
ord-77be761821ba4d1aa6f69789d251ffa9
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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