Potassium Carbonate → HCID 12083563, compound

HRID 1357240Notes

Reaction equation

HRID 1357240 reaction equation
[OH:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][NH:13][C:14]([C:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][C:17]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])[CH:6]=[CH:5]2.Br[CH2:37][C:38]#[N:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[C:38]([CH2:37][O:1][C:2]1[C:3]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][NH:13][C:14]([C:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][C:17]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])[CH:6]=[CH:5]2)#[N:39]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587379HCID 86587379, compound

Product 1

HCID 12083563HCID 12083563, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-5-p-tolyl-naphthalen-2-ylmethyl)-amide (252 mg, 0.54 mmol), prepared in the previous step, bromoacetonitrile (55 μL, 0.81 mmol) and potassium carbonate (378 mg, 2.73 mmol) in 15 mL of DMF was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was diluted with ethyl acetate, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced presure to give 2-butyl-benzofuran-3-carboxylic acid (6-cyanomethoxy-5-p-tolyl-naphthalen-2-ylmethyl)-amide (269 mg, 99%) as a light brown solid, mp 114-117° C.

Workup

  1. extractionextracted multiple times with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed

Sources & evidence

ORD record
ord-736c94cc676e4d368ea45531c8a326d8
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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