Diisobutylamine → 4-fluoro-N,N-diisobutyl-3-nitrobenzamide

HRID 883679노트

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HRID 883679 반응식
C(N=C=NC(C)C)(C)C.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].[CH2:23]([NH:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:24]([CH3:26])[CH3:25]>C1COCC1>[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:17])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

참가 물질

5

반응물 3

HCID 8085DiisobutylamineHCID 12734DiisopropylcarbodiimideHCID 679874-Fluoro-3-nitrobenzoic acid

생성물 1

HCID 607491584-fluoro-N,N-diisobutyl-3-nitrobenzamide수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

Diisopropylcarbodiimide (13.8 ml, 1.2 eq) is added to 4-fluoro-3-nitrobenzoic acid (15 g, 1 eq) in solution in THF (150 ml). The mixture is stirred for 3 hours at a temperature of approximately 20° C. then diisobutylamine (12.9 ml, 1 eq) is added. After stirring for 15 hours at approximately 20° C., the reaction mixture is evaporated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (70 ml). After decantation and extraction, the combined organic phases are washed with salt water, followed by drying over Na2SO4 then evaporating under reduced pressure at 40° C. Purification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2) produces the expected compound in the form of a yellow solid (13.8 g; 63% yield).

후처리

  1. stirringAfter stirring for 15 hours at approximately 20° C.
  2. customthe reaction mixture is evaporated under reduced pressure at 40° C
  3. extractionAfter decantation and extraction
  4. washthe combined organic phases are washed with salt water
  5. dry with materialby drying over Na2SO4
  6. customthen evaporating under reduced pressure at 40° C
  7. customPurification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2)

출처 및 근거

ORD 기록
ord-5f67905f78734948a28580205e21eda2
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236965B2

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