Lithium Hydroxide → Prt-062802

HRID 1944995Notes

Reaction equation

HRID 1944995 reaction equation
C1COCC1.C([O:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[NH:20])[N:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)C.[OH-].[Li+]>O>[CH3:18][N:17]([CH3:19])[C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([OH:21])=[O:8])=[CH:11][CH:12]=1)=[NH:20]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22631319ethyl 4-(N,N-dimethylamidino)benzoate

Product 1

HCID 4913141Prt-062802

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF solution of ethyl-4(N,N-dimethylcarbamimidoyl)benzoate (Q) was added an aqueous solution of lithium hydroxide (2 eq.) and the reaction mixture was stirred for 6 hours. The completion of the reaction was confirmed by HPLC. To the reaction mixture was added water, followed by extraction with ethyl acetate. The aqueous layer was acidified with 6N HCl to pH between 3-4 at which point the desired 4-(N,N-dimethylcarbamimidoyl)benzoic acid precipitated as the white solid. The white solid isolated was washed with hexane to afford 4-(N,N-dimethylcarbamimidoyl)benzoic acid as an hydrochloride salt (A).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customprecipitated as the white solid
  3. customThe white solid isolated
  4. washwas washed with hexane

Sources & evidence

ORD record
ord-32017d93cf71477a94666262c7c96a98
Source dataset
uspto-grants-2013_03
Patent number
US08394964B2

Reaction notes

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