Lithium Hydroxide → HCID 68293067, compound

HRID 514265Notes

Reaction equation

HRID 514265 reaction equation
[Cl:1][C:2]1[C:3]([C:18](=[O:23])[NH:19][CH:20]2[CH2:22][CH2:21]2)=[CH:4][C:5]2[N:9]=[C:8]([C:10]([O:12]C)=[O:11])[N:7]([CH:14]3[CH2:16][CH2:15]3)[C:6]=2[CH:17]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[C:3]([C:18](=[O:23])[NH:19][CH:20]2[CH2:21][CH2:22]2)=[CH:4][C:5]2[N:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]([CH:14]3[CH2:16][CH2:15]3)[C:6]=2[CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68293110HCID 68293110, compound

Product 1

HCID 68293067HCID 68293067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.65 g (4.9 mmol) of methyl 6-chloro-1-cyclopropyl-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylate were dissolved in 82 ml of THF and admixed at 0° C. with 0.24 g (9.89 mmol) of lithium hydroxide predissolved in 18 ml of water, and the reaction mixture was stirred at room temperature for 18 hours. The THF was distilled off and the aqueous phase was extracted three times with ethyl acetate; the aqueous phase was adjusted to pH=3 with HCl. The solid which precipitates out was filtered off with suction. Due to its relative instability, the acid was used for subsequent reactions without further purification.

Workup

  1. distillationThe THF was distilled off
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. customThe solid which precipitates out
  4. filtrationwas filtered off with suction
  5. customDue to its relative instability, the acid was used for subsequent reactions without further purification

Sources & evidence

ORD record
ord-590abc8386a14df2aa3716ec45422628
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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