Hydrochloric Acid → HCID 59497303, compound

HRID 1747382Notes

Reaction equation

HRID 1747382 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14](C(C)=C)[C:13]2=[O:24])[CH:4]=[C:3]1[CH3:25].O.Cl>C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:24])[CH:4]=[C:3]1[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59497610HCID 59497610, compound

Product 1

HCID 59497303HCID 59497303, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

(1,2-dimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (200 mg, 0.60 mmol) was suspended in ethanol (0.5 ml) and water (0.5 ml) and treated with 37% HCl (0.2 ml). The reaction was warmed to 60° C. for 1.5 h, cooled to room temperature and concentrated to low volume. The remaining residue was dissolved into DCM and sequentially washed with water and NaHCO3 (sat.). The organic phase was dried (MgSO4), filtered and concentrated to give 170 mg (97%) of 1-(1,2-dimethyl-1H-indol-7-ylmethyl)-1,3-dihydro-benzimidazol-2-one which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to low volume
  3. dissolutionThe remaining residue was dissolved into DCM
  4. washsequentially washed with water and NaHCO3 (sat.)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-274ae73ea89049608433d9b7a34a8b43
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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