Aluminum(III) Chloride → 3-Fluoro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

HRID 469349Notes

Reaction equation

HRID 469349 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[CH3:13][C:14]1[C:19]2[NH:20][C:21](=[O:23])[O:22][C:18]=2[CH:17]=[CH:16][CH:15]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[F:12][C:10]1[CH:11]=[C:3]([CH:4]=[C:5]([C:6]([C:16]2[CH:15]=[C:14]([CH3:13])[C:19]3[NH:20][C:21](=[O:23])[O:22][C:18]=3[CH:17]=2)=[O:7])[CH:9]=1)[C:1]#[N:2]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 219425933-Cyano-5-fluoro-benzoic acid chloride

Product 1

HCID 581811573-Fluoro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

Procedure

1.84 g (10.0 mmol) 3-cyano-5-fluoro-benzoic acid chloride, 1.49 g (10.0 mmol) 4-methyl-3H-benzoxazol-2-one and 5.33 g (40.0 mmol) aluminium trichloride were heated to 125° C. for 1.5 h with stirring. Then the mixture was mixed with ice water. The precipitate formed was suction filtered, washed with water and dried i. vac.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried i

Sources & evidence

ORD record
ord-41d6e11a255e4ff68354b328bb9e0a3d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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