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

HRID 525344ノート

反応式

HRID 525344 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ed2a8e0df88b46f7bec67b51af514ca4
出典データセット
uspto-grants-2016_05
特許番号
US09340549B2

反応ノート

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