Hydrochloric Acid → HCID 178487959, compound

HRID 1358569Notes

Reaction equation

HRID 1358569 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:26])[C:21]([O:23]CC)=[S:22])=[CH:15][CH:14]=3)[N:8]([CH3:27])[C:7]=2[CH:28]=1.O.[OH-].[K+].[OH-].[K+].[ClH:34]>O1CCCC1.CN(C)C=O.O>[ClH:34].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:26])[C:21]([OH:23])=[S:22])=[CH:15][CH:14]=3)[N:8]([CH3:27])[C:7]=2[CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 23719240Potassium hydroxide monohydrateHCID 86587626HCID 86587626, compound

Product 1

HCID 178487959HCID 178487959, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-[4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]-2-methylthiopropionate (2.0 g) in tetrahydrofuran (25 ml) were added successively potassium hydroxide monohydrate (0.42g), and dimethylformamide (5 ml). The mixture was stirred at room temperature for 2 hours. After addition of potassium hydroxide (0.42 g) and water (5 ml) the mixture was stirred at room temperature for 20 minutes. And then after addition of dimethylformamide (5 ml) the mixture was further stirred at room temperature for 1 hour and allowed to stand over night. To the reaction mixture was further added potassium hydroxide (0.42 g), water (5 ml) and dimethylformamide (5 ml) and the the mixture was stirred at 75° C. for 8 hours. The reaction mixture was poured into 1N hydrochloric acid (800 ml), stirred for 30 minutes and filtrated to give crystals. The crystals were washed successively with water, acetone and ethyl acetate and dried under reduced pressure to afford the title compound (1.27 g, mp 201-206° C.).

Workup

  1. stirringwas stirred at room temperature for 20 minutes
  2. stirringwas further stirred at room temperature for 1 hour
  3. waitto stand over night
  4. stirringthe the mixture was stirred at 75° C. for 8 hours
  5. stirringstirred for 30 minutes
  6. filtrationfiltrated
  7. customto give crystals
  8. washThe crystals were washed successively with water, acetone and ethyl acetate
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-d70e37d1bd824422ba50bed35d6eaf8a
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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