Acetonitrile → HCID 86749626, compound

HRID 863861Notes

Reaction equation

HRID 863861 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].[C:44](#N)[CH3:45]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:44]([C:5]([CH2:34][C:33]1[CH:36]=[CH:37][C:30]([C:22]2[O:21][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=2)=[CH:31][CH:32]=1)([C:4]([OH:3])=[O:20])[N:6]=[C:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:45]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Product 1

HCID 86749626HCID 86749626, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(diphenylmethylene)glycine ethyl ester (6.85 g; 25.6 mmol), 4-(benzoxazol-2-yl)benzyl bromide (7.37 g; 25.6 mmol), tetrabutylammonium bromide (0.83 g; 2.6 mmol); potassium carbonate (10.6 g; 77 mmol) and dry acetonitrile (50 ml) is heated at reflux 4 hours. The reaction is cooled and diluted with CH2Cl2, washed with water, dried (Na2SO4) and concentrated in vacuo to yield ethyl 2-[4-(benzoxazol-2yl)benzyl]-N-(diphenylmethylene)glycine as an oil which is used directly without further purification in Step B.

Workup

  1. temperatureat reflux 4 hours
  2. temperatureThe reaction is cooled
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bee5f53acf845038c1cb597b3497959
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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