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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
Notes
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Reaction equation

HRID 1747303 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-949755cc49364784b212f87a372c0740
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150556B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes