Dimethylformamide → 6-(2-bromo-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469311

反応式

HRID 469311 の反応式
S(Cl)(Cl)=O.CN(C=O)C.[Br:10][C:11]1[CH:16]=[C:15]([C:17]([OH:19])=O)[CH:14]=[CH:13][N:12]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:24][C:25]1[C:30]2[NH:31][C:32](=[O:34])[O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1.BrBr.ClCl>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[C:15]([C:17]([C:27]2[CH:26]=[C:25]([CH3:24])[C:30]3[NH:31][C:32](=[O:34])[O:33][C:29]=3[CH:28]=2)=[O:19])[CH:14]=[CH:13][N:12]=1

参加物

9

反応物 7

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24408BromineHCID 24526ChlorineHCID 2227012-Bromoisonicotinic acidHCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

生成物 1

HCID 581812136-(2-bromo-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

2.20 mL (30.0 mmol) thionyl chloride and 0.390 mL (4.80 mmol) DMF were added to 2.00 g (9.90 mmol) 2-bromopyridine-4-carboxylic acid in 30 mL DCM and refluxed for 2 h. The reaction mixture was evaporated to dryness and coevaporated twice with toluene. The residue was combined with 6.24 g (46.8 mmol) aluminium trichloride and 1.50 g (10.1 mmol) 4-methyl-3H-benzoxazol-2-one and the mixture obtained was stirred overnight at 110° C. and for 5 hours at 130° C. The mixture was decomposed with ice water and extracted twice with DCM. The organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE/MeOH and suction filtered. The product obtained is a mixture of the corresponding bromine and chlorine compound (40/60).

後処理

  1. temperaturerefluxed for 2 h
  2. customThe reaction mixture was evaporated to dryness
  3. customthe mixture obtained
  4. extractionextracted twice with DCM
  5. customThe organic phases were dried on magnesium sulphate
  6. filtrationfiltered
  7. customevaporated down i
  8. customThe residue was triturated with DIPE/MeOH and suction
  9. filtrationfiltered
  10. customThe product obtained

出典と根拠

ORDレコード
ord-a7869bb0c12f4d85aef225774e98f332
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

関連ノート

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