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Methanol → 1-(3-Carboxypropyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383966
Notes
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Reaction equation

HRID 1383966 reaction equation
O1CCCC1.CO.C([O:10][C:11]([CH2:13][CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=2[N:18]=[C:17]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:12])C.[OH-].[Li+]>C1(C)C=CC=CC=1.C(O)CCC.O>[C:11]([CH2:13][CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=2[N:18]=[C:17]1[CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)([OH:12])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 211886461-[3-(Ethoxycarbonyl)propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211885191-(3-Carboxypropyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 83.6%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

To a mixture of tetrahydrofuran (72 ml), methanol (24 ml), and water (24 ml), were added 1-[3-(ethoxycarbonyl)propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (2.0 g, 5.2 mmol) and lithium hydroxide (642 mg, 3 eq.). The resulting mixture was stirred overnight at room temperature and was then concentrated in vacuo to yield a white solid. This residue was taken into 250 ml of a 3:1 butanol:toluene solution. The organic fraction was washed once with 200 ml of water and then dried over magnesium sulfate. The solvents were removed in vacuo to yield 1.56 grams of tan solid, which was further purified by flash chromatography, eluting with a gradient solvent of 19:1 ethyl acetate:methanol to 9:1 ethyl acetate:methanol. The fractions containing the desired material were combined and concentrated under reduced pressure to yield 1.31 grams (70%) of the desired title product as a white solid.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customto yield a white solid
  3. washThe organic fraction was washed once with 200 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-069c737fd0bc4efbb552be01921490da
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06255494B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes