Aluminum(III) Chloride → 6-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469344Notes

Reaction equation

HRID 469344 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](Cl)=[O:10])[CH: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[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([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:10])[CH:3]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 190184816-Chloro-2-methylpyrimidine-4-carbonyl chloride

Product 1

HCID 581811186-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Procedure

2.48 g (13.0 mmol) 6-chloro-2-methyl-pyrimidine-4-carboxylic acid chloride, 1.94 g (13.0 mmol) 4-methyl-3H-benzoxazol-2-one and 6.93 g (52.0 mmol) aluminium trichloride were heated to 125° C. for 1.5 h with stirring. The mixture was combined with ice water and the precipitate formed was suction filtered and washed with water. Then the precipitate was dissolved in MeOH/DCM and filtered through silica gel suction. The filtrate was evaporated down and the residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down and triturated with diethyl ether. The precipitate was suction filtered, washed with diethyl ether and dried i. vac.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThen the precipitate was dissolved in MeOH/DCM
  5. filtrationfiltered through silica gel suction
  6. customThe filtrate was evaporated down
  7. customthe residue was purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down
  10. customtriturated with diethyl ether
  11. filtrationfiltered
  12. washwashed with diethyl ether
  13. customdried i

Sources & evidence

ORD record
ord-d2204886d6e64bdf90345ea72f8fe0d3
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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