Triethylamine → 2-(4-Bromomethyl-3-nitro-phenyl)-5-(4-chloro-phenyl)-[1,3,4]oxadiazole

HRID 1360803Notes

Reaction equation

HRID 1360803 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][Br:18])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=2)=O)=[CH:4][CH:3]=1.CCN(CC)CC>ClCCCl>[Br:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[O:22][C:6]([C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)=[CH:12][C:13]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 669668063-nitro-4-bromomethyl-benzoic acid N'-(4-chloro-benzoyl)-hydrazide

Product 1

HCID 669664172-(4-Bromomethyl-3-nitro-phenyl)-5-(4-chloro-phenyl)-[1,3,4]oxadiazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a 100 mL round-bottom flask was added 2.1 g (12.3 mmol) of 4-chlorobenzoic acid hydrazide, 3.20 g (12.3 mmol) of 4-bromomethyl-3-nitro benzoic acid, 3.54 g (18.5 mmol) of EDC, and 200 mL of DCM. Allowed to stir at room temperature for 18 h. Removed ⅔ of DCM, added water and filtered off white solid and washed with Et2O to give 3-nitro-4-bromomethyl-benzoic acid N′-(4-chloro-benzoyl)-hydrazide as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.99 (s, 1H) 5.12 (s, 1H) 7.59-7.64 (m, 2H) 7.91-7.95 (m, 2H) 7.96 (d, J=8.21 Hz, 1H) 8.22-8.29 (m, 1H) 8.57 (dd, J=6.57, 1.77 Hz, 1H) 10.76 (s, 1H) 10.94 (dd, J=5.18, 0.88 Hz, 1H). MS (m/z) 413.9 M (+1), tR=1.28, Meth 10. To a 500 mL round-bottom flask was added 4.95 g (12.0 mmol) of 3-nitro-4-bromomethyl-benzoic acid N′-(4-chloro-benzoyl)-hydrazide, 6.09 g (36.0 mmol) DMC, and 100 mL of DCE. To this pale yellow solution was added 6.70 mL (48.0 mmol) of Et3N, slowly over 5 min. The dark green solution was allowed to stir at 40° C. for 30 min. then cooled to room temperature stirred for 18 h. Removed solvent and purified over a silica plug 10-30% EtOAc/Hep to give the title compound as yellow solid. MS (m/z) 350.0 M (+1), retention time=1.51, Method 10.

Workup

  1. temperaturethen cooled to room temperature
  2. stirringstirred for 18 h
  3. customRemoved solvent and purified over a silica plug 10-30% EtOAc/Hep

Sources & evidence

ORD record
ord-2c21267ff51c4c89a634583970169572
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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