Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate → Methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

HRID 349128

反応式

HRID 349128 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cu][C:22]#[N:23]>CN1CCCC1=O>[C:22]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:23]

参加物

4

反応物 2

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 21086168Methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (Preparation 3) (0.15 g), copper (I) cyanide, and N-methylpyrrolidinone (1 mL) was heated at 150° C. overnight, at which time the mixture was cooled and partitioned between ethyl acetate and aq. HCl (1N). The organic layer was dried (magnesium sulfate), concentrated under reduced pressure, and the residue was chromatographed on silica gel using ethyl acetate-hexane (20/80) to give 0.066 g of the desired product. ms (m+H) 289.2. See also preparation 7 for the preparation of the acid.

後処理

  1. temperaturewas cooled
  2. custompartitioned between ethyl acetate and aq. HCl (1N)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-9f535ef1d5a1403ea013533876849b4b
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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