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4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]-3-methylureido}ethyl ester

HRID 899132
Notes
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Reaction equation

HRID 899132 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][OH:17])[C:11]([NH:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][O:17][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[C:11]([NH:13][CH3:14])=[O:12])=[CH:18][CH:19]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 690720791-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3-methylureaHCID 178418339Butyllithium

Product 1

HCID 86616243Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]-3-methylureido}ethyl esterYield 12.7%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

To a well-stirred solution of 1-[2-(4-cyanophenoxy)ethyl]-1-(2-hydroxy-ethyl)-3-methylurea (6.6 g, 0.0257 mol; see step (i) above) in dry THF (70 mL) was added n-BuLi (2.85 N, 1.766 g, 0.0276 mol) at −78° C., dropwise under a nitrogen atmosphere. After stirring at the same temperature for 45 min, p-toluenesulfonyl chloride (5.25 g, 0.0276 mol) in dry THF was added (drop by drop) and the reaction mixture was then stirred at −40° C. for 2 h. The reaction was quenched with 50 mL water and warmed to room temperature. The product was extracted with ethyl acetate, washed with brine solution and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography over silica gel (using 15-25% methanol in chloroform) yielded 1.36 g of the title compound as a brown gummy liquid.

Workup

  1. stirringthe reaction mixture was then stirred at −40° C. for 2 h
  2. customThe reaction was quenched with 50 mL water
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with brine solution
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-d887d000e981418f99ffb3abff582464
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07354917B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes