Triethylamine → N-ethyl-5-(2-nitrophenyl)-1,3,4-oxadiazol-2-amine

HRID 1041752Notes

Reaction equation

HRID 1041752 reaction equation
[CH2:1]([NH:3][C:4](=[O:18])[NH:5][NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[CH3:2].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([NH:3][C:4]1[O:18][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[N:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 472526074-Ethyl-1-(2-nitrobenzoyl)semicarbazide

Product 1

HCID 67264620N-ethyl-5-(2-nitrophenyl)-1,3,4-oxadiazol-2-amineYield 61.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-ethyl-1-(2-nitrobenzoyl)semicarbazide (4 g) in DCM (30 mL) was treated with triethyl amine (12 mL), PTS-Cl (4.8 g) and DMAP (100 mg). The reaction mixture was stirred for 4 hours, concentrated, and purified by silica gel chromatography to afford 2.3 g of ethyl-(5-(2-nitro-phenyl)-(1,3,4)oxadiazol-2-yl)-amine: 1H NMR (300 MHz, CDCl3) δ 8.1 (dd, 1H), 8.0 (d, 1H), 7.8 (m, 2H), 4.9 (bs, 1H), 3.6 (q, 2H), 1.4 (t, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e80e3622416f47e7ae0da8216412e1cc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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