Hydrochloric Acid → HCID 59497358, compound

HRID 1747349Notes

Reaction equation

HRID 1747349 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8](C(C)=C)[C:7]1=[O:18].Cl>C(O)C.O.ClCCl>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:18]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59497548HCID 59497548, compound

Product 1

HCID 59497358HCID 59497358, compoundYield 86.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-(3-Isopropenyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (4.8 g, 18.4 mmol) in ethanol (30 ml) and water (30 ml) was added 37% hydrochloric acid (24 ml). The resulting solution was warmed to 60° C. for twenty minutes and cooled. The reaction was diluted with dichloromethane and water. The layers were separated and the organic phase was dried (Na2SO4), filtered and concentrated to give 3.5 g (86%) of the desired product as an oil which solidified on standing. Used without further purification.

Workup

  1. temperaturecooled
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0a89cf2edb14a2bbeb4955d9e7b8a24
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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