Methyl N-(triethylammoniosulfonyl)carbamate → 4-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-nitroaniline

HRID 1513262Notes

Reaction equation

HRID 1513262 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=O)=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[O:19][C:6]([C:5]3[CH:20]=[CH:21][C:2]([NH2:1])=[C:3]([N+:22]([O-:24])=[O:23])[CH:4]=3)=[N:8][N:9]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 271692284-methoxybenzoic acid N'-(4-amino-3-nitrobenzoyl)-hydrazide

Product 1

HCID 669667784-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methoxybenzoic acid N′-(4-amino-3-nitrobenzoyl)-hydrazide (750 mg, 2.27 mmol) and Burgess reagent (1.62 g, 6.81 mmol) in THF (15 mL) was microwaved at 150° C. for 20 min. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (heptane/EtOAc=1:3) to give the title compound as a yellow solid. MS: m/z 313 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (heptane/EtOAc=1:3)

Sources & evidence

ORD record
ord-00f7b707af98449ea325f5700fdf055b
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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