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

HRID 14339

반응식

HRID 14339 반응식
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]

참가 물질

4

반응물 2

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoateHCID 178418546HCID 178418546, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1a91c3195d9c448497bee984f21dcaae
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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