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Hydrochloric Acid → 1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

HRID 1747303
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HRID 1747303 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([CH3:23])[C:20]([CH3:22])=[CH:21][C:16]=3[N:15](C(C)=C)[C:14]2=[O:27])=[CH:3]1.O.Cl>CO.C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([CH3:23])[C:20]([CH3:22])=[CH:21][C:16]=3[NH:15][C:14]2=[O:27])=[CH:3]1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 594974911-(1,4-Dimethyl-1H-indol-3-ylmethyl)-3-isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

생성물 1

HCID 594974211-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

시약·촉매·용매 2

HCID 887Methanol용매
HCID 6344
Dichloromethane
용매

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온도
60 °C

실험 절차

To 1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-3-isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one (0.35 mmol) in MeOH (5 mL) was added water (5 mL) and cone. HCl (3 mL). The reaction mixture was heated to 60° C. for 2 h. The reaction mixture turned into pink in color and heterogeneous (milky solution). The TLC indicated that the reaction was complete and clean. The reaction mixture was therefore diluted with CH2Cl2 and washed with water. The organic phase remained heterogeneous (milky with fine powder). The organic phase was filtered through a fine filter to collect some of the solid which was partially soluble in DMSO-d6. 1H-NMR indicated this filtered solid being the desired product. Therefore, the organic phase was concentrated without drying with Na2SO4 to afford a pink solid. 1H-NMR of this product in DMSO-d6 matched well with the previous filtered solid.

후처리

  1. washwashed with water
  2. filtrationThe organic phase was filtered through
  3. filtrationa fine filter
  4. customto collect some of the solid which
  5. concentrationTherefore, the organic phase was concentrated
  6. dry with materialwithout drying with Na2SO4
  7. customto afford a pink solid
  8. filtrationprevious filtered solid

출처 및 근거

ORD 기록
ord-949755cc49364784b212f87a372c0740
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150556B2

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