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Lithium hydroxide, monohydrate → 2-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid

HRID 349480
Notes
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Reaction equation

HRID 349480 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[NH:10][C:9]=2[C:8]([OH:22])=[CH:7][CH:6]=1)=[O:4].O[Li].O>C1COCC1.CO.O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:11]1[NH:10][C:9]2[C:8]([OH:22])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=2[N:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 691323632-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid methyl ester

Product 1

HCID 691199912-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 22242641
Methanol--water (1/1)
Solvent

Procedure

Wang resin-supported 2-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid methyl ester (570 mg, 0.47 mmol) obtained in step 5 was dissolved in THF, LiOH.H2O (99 mg, 2.35 mmol) in MeOH—H2O (2:1) was added thereto and the resulting mixture was refluxed for 5 hours. The resulting solution was cooled to room temperature and filtered. The filtrate was washed with MeOH and CH2Cl2, and dried to obtain the title compound (551 mg, 0.42 mmol) in a yield of 90%.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with MeOH and CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-5c087ac937d64aad9daa6fcf0fa59b64
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179832B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes