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

HRID 469311

반응식

HRID 469311 반응식
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

참가 물질

9

반응물 7

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7869bb0c12f4d85aef225774e98f332
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629137B2

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