Methyl N-(triethylammoniosulfonyl)carbamate → 2-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole

HRID 419336Notes

Reaction equation

HRID 419336 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=1)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:1][CH2:2][C:3]1[O:19][C:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:5]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59452892N'-(chloroacetyl)-3-(methyloxy)-4-nitrobenzohydrazide

Product 1

HCID 594526612-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N′-(Chloroacetyl)-3-(methyloxy)-4-nitrobenzohydrazide (1.00 g, 3.48 mmol) and Burgess' reagent (0.994 g, 4.17 mmol) in THF (15 mL) was heated to 120° C. for 20 minutes in the microwave. The reaction was complete by TLC. Purification by flash chromatography provided the title compound (0.802 g, 2.93 mmol, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.04 (s, 3H), 5.16 (s, 2H), 7.72 (dd, J=8.4, 1.8 Hz, 1H), 7.84 (d, J=1.8 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-3db04b64321345e3ae82777965e9b2cd
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…