Acetamide → HCID 21188002, compound

HRID 1383431Notes

Reaction equation

HRID 1383431 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH2:29])(=O)C.B(F)(F)F.CCOCC>C1(C)C(C)=CC=CC=1>[CH2:19]([O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[N:29]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 21188000HCID 21188000, compound

Product 1

HCID 21188002HCID 21188002, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.46 g of 2-benzyloxy-1-(2-benzyloxy-phenyl)-ethanone according to step (c) are refluxed with 2.95 g of acetamide and 0.9 ml of boron trifluoride etherate in 100 ml of anhydrous xylene over 20 hours. After the solution obtained has been cooled and washed with water it is dried over sodium sulphate, the solvent is distilled off in vacuo and the residue remaining is chromatographed on silica gel (toluene). In addition to re-isolated educt, 1 g (31%) of the target compound is isolated.

Workup

  1. customAfter the solution obtained
  2. temperaturehas been cooled
  3. washwashed with water it
  4. dry with materialis dried over sodium sulphate
  5. distillationthe solvent is distilled off in vacuo
  6. customthe residue remaining is chromatographed on silica gel (toluene)
  7. additionIn addition
  8. customto re-isolated educt

Sources & evidence

ORD record
ord-1c1abfde5e0b4d6eb13bfa09a86fa2ce
Source dataset
uspto-grants-2001_07
Patent number
US06255327B1

Reaction notes

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