1,2-Dichloroethane → HCID 666146, compound

HRID 533714Notes

Reaction equation

HRID 533714 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([C:12]3[CH:20]=[CH:19][C:15](C(O)=O)=[CH:14][CH:13]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N([OH:34])N=NC=2C=1.CC[N:37]([CH:41](C)C)C(C)C.CC(C)(C)CCN>CN(C=O)C.O>[C:1]1([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:19][C:20]=3[C:41]([NH2:37])=[O:34])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 197093,3-DimethylbutylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 125192934-(3-Phenyl-1,2,4-oxadiazol-5-yl)benzoic acid

Product 1

HCID 666146HCID 666146, compoundYield 124.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoic acid (200 mg, 0.75 mmol) in DMF (2 mL) was added EDC (167 mg, 0.90 mmol), HOBt (122 mg, 0.90 mmol), DIPEA (200 mg, 1.50 mmol) and 3,3-dimethylbutylamine (113 mg, 1.12 mmol). The reaction was stirred at room temperature for 18 h. The reaction was diluted with water (10 mL) and isolated the white precipitate by vacuum filtration to afford N-(3,3-dimethylbutyl)-4-(3-phenyl-1,2,4-oxadiazol-5-yl-benzamide (248 mg, 95%). 1H-nmr (400 MHz, CDCl3) δ 8.31 (d, J=8 Hz, 2H), 8.23-8.17 (m, 2H), 7.95 (d, J=8 Hz, 2H), 7.59-7.52 (m, 3H), 6.12 (s, 1H), 3.57-3.51 (m, 2H) 1.62-1.58 (m, 2H), 1.02 (s, 9H); MS (ESI) m/z 349.9.

Workup

  1. customisolated the white precipitate
  2. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-9fa148ac26414a3e87b187ae5e5af6c6
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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