Potassium Carbonate → 3-[(6-Bromohexyl)oxy]benzenecarboxamide

HRID 415568

반응식

HRID 415568 반응식
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CC#N>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:7][C:8]1[CH:9]=[C:10]([C:11]([NH2:13])=[O:12])[CH:14]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 3424033-Hydroxybenzamide

생성물 1

HCID 594029303-[(6-Bromohexyl)oxy]benzenecarboxamide수율 67%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

(Method D) K2CO3 (1.38 g, 10 mmol, 1 equiv.) was added to a suspension of 3-hydroxybenzamide (1.37 g, 10 mmol, 1 equiv.) in CH3CN (100 ml). The mixture stirred for 10 min at room temperature, before 1,6-dibromo-hexane (9.76 g, 40 mmol, 4 equiv.) was added. The resulting mixture was stirred at 60° C. for 16 h. After this time, the reaction was cooled to room temperature, any undissolved solids were filtered off and the filtrate evaporated under reduced pressure to dryness. The residue was taken-up in EtOAc and water. The organic phase was separated and washed consecutively with K2CO3 solution, water and brine. Dried with MgSO4 and evaporated under reduced pressure to a small volume. The precipitant solid was filtered and washed with EtOAc/pentane, to give the desired compound as a white solid (2.0 g, 67%), mp 115-117° C. HPLC-MS (method 1): m/z 300 [M]+, 302 [M+2H]+, Rt=4.08 min.

후처리

  1. additionwas added
  2. temperatureAfter this time, the reaction was cooled to room temperature
  3. filtrationany undissolved solids were filtered off
  4. customthe filtrate evaporated under reduced pressure to dryness
  5. customThe organic phase was separated
  6. washwashed consecutively with K2CO3 solution, water and brine
  7. dry with materialDried with MgSO4
  8. customevaporated under reduced pressure to a small volume
  9. filtrationThe precipitant solid was filtered
  10. washwashed with EtOAc/pentane

출처 및 근거

ORD 기록
ord-cab0fd9a957e427797afc213ab8967fb
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088791B2

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