Acetone → 1,3-dihydro-1-(4-oxocyclohexyl)-2H-benzimidazol-2-one

HRID 525344노트

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HRID 525344 반응식
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]3=[O:20])[CH2:7][CH2:6]2)[O:4]CC1.CC(C)=O.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 207659343-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-benzimidazol-2-one

생성물 1

HCID 214716841,3-dihydro-1-(4-oxocyclohexyl)-2H-benzimidazol-2-one수율 74.2%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a flask charged with 1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-benzo[d]imidazol-2(3H)-one (1.100 g, 4.01 mmol) were added acetone (7.29 mL) and water (0.729 mL) followed by PPTS (1.310 g, 5.21 mmol). The resulting light brown solution was heated at reflux overnight. Water was then added to the mixture leading to an oiling out of the organics. The mixture was transferred to a separatory funnel and extracted with EtOAc (2×). The combined organic layers were dried with Na2SO4, filtered, and dried under reduced pressure. The oil thus obtained was purified with a 50 g SNAP column (Biotage) ramping DCM:MeOH:NH4OH (90:10:1) in DCM from 0-35% leading to coelution of product and starting material. The mixture was used in the next step without further purification. The mixture containing 1-(4-oxocyclohexyl)-1H-benzo[d]imidazol-2(3H)-one (0.685 g, 2.97 mmol, 74.2% yield) was obtained as a brown foam. m/z (ESI) 231.2 (M+H)+.

후처리

  1. temperatureThe resulting light brown solution was heated
  2. temperatureat reflux overnight
  3. customThe mixture was transferred to a separatory funnel
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customThe oil thus obtained
  9. customwas purified with a 50 g SNAP column (Biotage)
  10. customThe mixture was used in the next step without further purification

출처 및 근거

ORD 기록
ord-ed2a8e0df88b46f7bec67b51af514ca4
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

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