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Water → 2-{[2-(4-{2-[(2-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}-benzoic acid

HRID 898932
Notes
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Reaction equation

HRID 898932 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:29][CH3:30])[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22]C)=[O:21])=[CH:11][CH:10]=1.O.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:29][CH3:30])[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][S:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([OH:22])=[O:21])=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 69259897Methyl 2-{[2-(4-{2-[(2-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoate

Product 1

HCID 102547322-{[2-(4-{2-[(2-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}-benzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Methyl 2-{[2-(4-{2-[(2-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}-benzoate was dissolved in a mixture of THF (freshly distilled)/water (2/1, 3 ml), Lithium hydroxide (0.015 g, 0.629 mmol) was added. The reaction was performed in a single node microwave oven (5 min, 150 deg). THF was removed by evaporation. Water was added (10 ml) and the basic water phase was washed with diethyl ether (2×10 ml). Addition of HCl (2 ml, 1 M, pH 1). The water phase was extracted with two portions of DCM (20 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.103 g of 2-{[2-(4-{2-[(2-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}-benzoic acid (yield 95.5%).

Workup

  1. additionwas added
  2. customThe reaction was performed in a single node microwave oven
  3. custom(5 min, 150 deg)
  4. customTHF was removed by evaporation
  5. additionWater was added (10 ml)
  6. washthe basic water phase was washed with diethyl ether (2×10 ml)
  7. additionAddition of HCl (2 ml, 1 M, pH 1)
  8. extractionThe water phase was extracted with two portions of DCM (20 ml)
  9. dry with materialThe organic phase was dried (MgSO4)
  10. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-16b6463782274303a237f59afd2d72d9
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes