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Water → 2-[4-(4-cyano-benzyloxy)-phenoxy]-N-methyl-acetamide

HRID 853149
Notes
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Reaction equation

HRID 853149 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([NH:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.O>CC(=O)CC>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)=[CH:23][CH:24]=1)#[N:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 181839132-(4-hydroxyphenoxy)-N-methylacetamide

Product 1

HCID 115510952-[4-(4-cyano-benzyloxy)-phenoxy]-N-methyl-acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

A solution of 500 mg of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide in 25 ml of 2-butanone was treated with 762 mg of potassium carbonate and 595 mg of 4-bromomethyl-benzonitrile. The reaction mixture was stirred at room temperature for 60 h. For the working-up, the reaction mixture was treated with water, then extracted with ethyl acetate. The aqueous layer was re-extracted with ethyl acetate, the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in ether and the crystals obtained were collected on a filter funnel. After drying there were obtained 744 mg (95% of theory) of 2-[4-(4-cyano-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=297 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated in ether
  6. customthe crystals obtained
  7. customwere collected on a filter funnel
  8. customAfter drying there

Sources & evidence

ORD record
ord-66053ca26778471a84b55fc423afebb3
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253318B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes