4-Methylmorpholine → 3-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

HRID 2053761ノート

反応式

HRID 2053761 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CN1CCOCC1>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:6])[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 68513Bromoterephthalic acid

生成物 1

HCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

100 g (0.388 mol) of 2-bromoterephthalic acid is dissolved in 700 mL of N,N-dimethylformamide and slowly combined with 69.2 g (0.427 mol) of N,N′-carbonyldiimidazole with stirring. After total dissolution, the mixture is stirred for 15 minutes at ambient temperature and then 48.5 mL (0.582 mol) of pyrrolidine and 93.9 mL (0.854 mol) of N-methylmorpholine are slowly added dropwise one after the other. The mixture is stirred for 2.5 days at ambient temperature and then concentrated in vacuo. The residue is combined with distilled water and acidified with 2 molar hydrochloric acid solution. The aqueous phase is extracted with ethyl acetate. The precipitate formed is suction filtered and dried at 40° C. Yield: 29.4 g (25%); Rf value: 0.30 (silica gel; dichloromethane/ethanol=9:1); C12H12BrNO3 (298.14); mass spectrum: (M+H)+=298/300 (bromine isotope).

後処理

  1. dissolutionAfter total dissolution
  2. stirringthe mixture is stirred for 15 minutes at ambient temperature
  3. stirringThe mixture is stirred for 2.5 days at ambient temperature
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. customThe precipitate formed
  7. filtrationfiltered
  8. customdried at 40° C

出典と根拠

ORDレコード
ord-e516b1851eda4a3ab51ad14884abd9a5
出典データセット
uspto-grants-2008_02
特許番号
US07326791B2

反応ノート

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