1,2-Dichloroethane → Methyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate

HRID 533712Notes

Reaction equation

HRID 533712 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.O[NH:38][C:39](=[NH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(#N)C.O>[C:40]1([C:39]2[N:46]=[C:6]([C:5]3[CH:4]=[CH:3][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:10][CH:9]=3)[O:8][N:38]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 36144541,4-Benzenedicarboxylic acid, methyl esterHCID 178513281HCID 178513281, compound

Product 1

HCID 851434Methyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoateYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of mono-methyl terephthalate (1.50 g, 8.33 mmol) in acetonitrile (16 mL) was added EDC (4.65 g, 25.0 mmol), HOBt (1.12 g, 8.33 mmol), DIPEA (3.24 g, 25.0 mmol) and N-hydroxybenzimidamide (1.36 g, 10.0 mmol). The reaction was heated at 100° C. for 30 mins in a microwave. The reaction was then cooled to rt, diluted with water (60 mL) and isolated the crude white precipitate by vacuum filtration. Dissolved in CH2Cl2 and passed through a plug of silica to afford methyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate as an off-white solid (640 mg, 23%). 1H-nmr (400 MHz, CDCl3) δ 8.33 (d, J=8 Hz, 2H), 8.24 (d, J=8 Hz, 2H), 8.21-8.11 (m, 2H), 7.59-7.51 (m, 3H), 4.00 (s, 3H); MS (ESI) m/z 280.9

Workup

  1. temperatureThe reaction was then cooled to rt
  2. customisolated the crude white precipitate
  3. filtrationby vacuum filtration
  4. dissolutionDissolved in CH2Cl2

Sources & evidence

ORD record
ord-7065c615cc5a47a8be5a2e058a305aee
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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