Acetamide → HCID 86689662, compound

HRID 1622993Notes

Reaction equation

HRID 1622993 reaction equation
B(F)(F)F.CCOCC.[CH2:10]([O:17][C:18]1[CH:36]=[CH:35][C:21]([C:22]([O:24][CH2:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)=O)=O)=[CH:20][CH:19]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C([NH2:40])(=O)C>C(Cl)Cl>[Br:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[N:40]=[C:22]([C:21]3[CH:35]=[CH:36][C:18]([O:17][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=3)[O:24][CH:25]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 86689663HCID 86689663, compound

Product 1

HCID 86689662HCID 86689662, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To boron trifluoride etherate (0.322 mL, 2.5 mmol) was added 2-(4-bromophenyl)-2-oxoethyl 4-(heptyloxy)benzoate (1.0 g, 2.3 mmol) and acetamide (4.91 g, 83.0 mmol) in DCM (10 mL). The reaction mixture was heated to 50° C. then 140° C. for 16 h, DCM was distilled off. The reaction mixture was cooled, diluted with acetonitrile and stirred at RT for 1 h. The precipitate was isolated by filtration to afford 273 mg (23%) of 4-(4-bromophenyl)-2-(4-(heptyloxy)phenyl)oxazole as a brown solid. LCMS-ESI (m/z) calculated for C22H24BrNO2: 414.3; found 414.0 [M+H]+, tR=3.00 min. (Method 4).

Workup

  1. distillationDCM was distilled off
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with acetonitrile
  4. customThe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-a355adef7a5f4dc995c01db00ebef371
Source dataset
uspto-grants-2014_07
Patent number
US08778923B2

Reaction notes

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