2(3H)-Benzoxazolone → HCID 58181175, compound

HRID 469308Notes

Reaction equation

HRID 469308 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20].[Cl-].[Cl-].[Cl-].[Al+3]>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:17]2[CH:18]=[CH:19][C:14]3[NH:13][C:12](=[O:20])[O:11][C:15]=3[CH:16]=2)=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 6451240Aluminum(III) ChlorideHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58181175HCID 58181175, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.93 g (22.2 mmol) 6-chloropyrimidine-4-carboxylic acid chloride, 3.00 g (22.2 mmol) 2-benzoxazolinone and 14.8 g (111 mmol) aluminium trichloride were combined and heated for 3 h to 130° C. Then the mixture was combined with ice water and EtOAc, the solid was suction filtered and the phases were separated. The aqueous phase was extracted twice with EtOAc, the organic phases were combined, dried and evaporated down. The residue was triturated in DIPE, suction filtered and dried.

Workup

  1. temperatureheated for 3 h to 130° C
  2. filtrationfiltered
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted twice with EtOAc
  5. customdried
  6. customevaporated down
  7. customThe residue was triturated in DIPE, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-7f317400a94f4731beca3addce9bab6a
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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