Aluminum(III) Chloride → HCID 58181174, compound

HRID 469346Notes

Reaction equation

HRID 469346 reaction equation
CC1C2NC(=O)OC=2C=CC=1.[Cl-:12].[Cl-].[Cl-].[Al+3].Cl[C:17]1[C:22]([CH3:23])=[C:21]([C:24]([C:26]2[CH:35]=[C:34]([CH3:36])[C:29]3[NH:30][C:31](=[O:33])[O:32][C:28]=3[CH:27]=2)=[O:25])[CH:20]=[CH:19][N:18]=1>>[Cl:12][C:19]1[CH:20]=[C:21]([C:24]([C:26]2[CH:35]=[C:34]([CH3:36])[C:29]3[NH:30][C:31](=[O:33])[O:32][C:28]=3[CH:27]=2)=[O:25])[C:22]([CH3:23])=[CH:17][N:18]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 86651864HCID 86651864, compound

Product 1

HCID 58181174HCID 58181174, compound

Conditions

Temperature
125 °C

Procedure

1.53 g (10.0 mmol) 3-methyl-1-oxy-isonicotinic acid were stirred with 9.32 mL (100 mmol) phosphorus oxychloride and boiled for 4 h. The reaction mixture was evaporated to dryness i. vac. and coevaporated twice with toluene. The crude product thus obtained (which was present in admixture with 2-chloro-3-methyl-isonicotinic acid chloride) was combined with 1.49 g (10.0 mmol) 4-methyl-3H-benzoxazol-2-one and 5.33 g (40.0 mmol) aluminium trichloride and heated to 125° C. for 1.5 h with stirring. Then the mixture was mixed with ice water and the precipitated grease was separated from the solvent by decanting. The residue was triturated with MeOH. The precipitate formed was suction filtered, washed with MeOH and diethyl ether and dried i. vac. The product thus obtained, which was present in admixture with 6-(2-chloro-3-methyl-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one, was reacted further without further purification.

Workup

  1. customthe precipitated grease was separated from the solvent
  2. customby decanting
  3. customThe residue was triturated with MeOH
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed with MeOH and diethyl ether
  7. customdried i
  8. customThe product thus obtained
  9. customwas reacted further without further purification

Sources & evidence

ORD record
ord-65737e75231c4be483294a30661ef557
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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