Hydrochloric Acid → 1-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-5-methyl-1,3-dihydro-benzimidazol-2-one

HRID 1747313Notes

Reaction equation

HRID 1747313 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=4[N:14](C(C)=C)[C:13]3=[O:25])[CH:10]=1)[N:7]([CH3:26])[C:6]([CH3:27])=[C:5]2[CH3:28].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=4[NH:14][C:13]3=[O:25])[CH:10]=1)[N:7]([CH3:26])[C:6]([CH3:27])=[C:5]2[CH3:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 594976701-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-5-methyl-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594972831-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-5-methyl-1,3-dihydro-benzimidazol-2-oneYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-5-methyl-1,3-dihydro-benzimidazol-2-one (60 mg, 0.15 mmol) in a mixture of MeOH (3 mL) and water (3 mL), was added 1N HCl (2 mL). The reaction mixture was heated to 60° C. for 2 h. When the reaction was completed, the mixture was extracted with CH2Cl2 (×2). The organic phase was dried over Na2SO4 and concentrated to afford 40 mg of the desired product. The resulting residue was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (×2)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8c202d327409420a9f1a5dbd969b9d24
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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