Hydrochloric Acid → HCID 178503098, compound

HRID 1358572Notes

Reaction equation

HRID 1358572 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]2[CH:8]=[C:9]([S:12][CH3:13])[CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:28])[C:24]([O:26]C)=[S:25])=[CH:18][CH:17]=1.Cl>O1CCOCC1>[ClH:1].[CH3:2][N:3]1[C:7]2[CH:8]=[C:9]([S:12][CH3:13])[CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:28])[C:24]([OH:26])=[S:25])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18184947HCID 18184947, compound

Product 1

HCID 178503098HCID 178503098, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 3-[4-(1-methyl-6-methylthio-1H-benzimidazol-2-ylmethoxy)phenyl]-2-methylthiopropionate hydrochloride (5.75 g), concentrated hydrochloric acid (100 ml) and 1,4-dioxane (100 ml) was heated at reflux for 90 minutes. The reaction mixture was concentrated to dryness. To the residue was added tetrahydrofuran and the mixture was irradiated with ultrasonic waves. The insoluble material was isolated by filtration, washed with ethyl acetate, dissolved in N,N-dimethylformamide and reprecipitated with ether to afford the title compound (5.02 g, mp 193-196° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes
  3. concentrationThe reaction mixture was concentrated to dryness
  4. additionTo the residue was added tetrahydrofuran
  5. customthe mixture was irradiated with ultrasonic waves
  6. customThe insoluble material was isolated by filtration
  7. washwashed with ethyl acetate
  8. dissolutiondissolved in N,N-dimethylformamide
  9. customreprecipitated with ether

Sources & evidence

ORD record
ord-9e5e573de72d40779ebb0ca209b05cbd
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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