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

HRID 2096359Notes

Reaction equation

HRID 2096359 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:15][C:16]1[C:21]2[NH:22][C:23](=[O:25])[O:24][C:20]=2[CH:19]=[CH:18][CH:17]=1>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:18]2[CH:17]=[C:16]([CH3:15])[C:21]3[NH:22][C:23](=[O:25])[O:24][C:20]=3[CH:19]=2)=[O:9])[CH:3]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Procedure

2.34 g (13.2 mmol) 6-chloropyrimidine-4-carbonyl chloride, 8.00 g (60.0 mmol) aluminium trichloride and 1.79 g (12.0 mmol) 4-methyl-3H-benzoxazol-2-one were heated to 130° C. for 1.5 h. After cooling to RT the mixture was mixed with ice water, then extracted with ethyl acetate, the organic phase was dried on sodium sulphate and evaporated down i.vac. The crude product left as a solid was triturated with diethyl ether, suction filtered and dried in the air.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was dried on sodium sulphate
  3. customevaporated down i.vac
  4. waitThe crude product left as a solid
  5. customwas triturated with diethyl ether, suction
  6. filtrationfiltered
  7. customdried in the air

Sources & evidence

ORD record
ord-8c13c75b1f6f40a89ba3759d10f2ec5f
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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