1,2-Dichloroethane → HCID 59002672, compound

HRID 467552Notes

Reaction equation

HRID 467552 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[CH:15][N:16]=2)=[CH:8][C:7]=1[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.C(Cl)CCl.CCOC(C)=O>C(Cl)Cl>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[CH:15][N:16]=2)=[CH:8][C:7]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:1](=[O:4])[CH3:2])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 58992419HCID 58992419, compound

Product 1

HCID 59002672HCID 59002672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into an 8 ml sealed tube, was placed acetic acid (48 mg, 0.80 mmol). This was followed by the addition of a solution of 2′-Methyl-5′-oxazol-2-yl-biphenyl-4-ylamine (100 mg, 0.40 mmol) in CH2Cl2 (2 g) with stirring for 10 mins in a bath of H2O/ice. This was followed by the addition of a solution of EDC (90 mg, 0.47 mmol) in CH2Cl2 (2 g). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE=1:1). The resulting mixture washed 3 times with 10 ml of HCl(10%), 3 times with 10 ml of sat.NaHCO3 and 3 times with 10 ml of H2O. The organic layer was dried over Na2SO4. Removal of the solvents under reduced pressure afforded the title compound, N-(2′-Methyl-5′-oxazol-2-yl-biphenyl-4-yl)-acetamide, as a yellow solid (82 mg, 70%).

Workup

  1. customInto an 8 ml sealed tube
  2. customto react
  3. washThe resulting mixture washed 3 times with 10 ml of HCl(10%), 3 times with 10 ml
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-13f1967e5d314fc38bbb1260bf56c0c8
Source dataset
uspto-grants-2014_01
Patent number
US08623871B2

Reaction notes

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