Tetrahydrofuran → 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine

HRID 1360795Notes

Reaction equation

HRID 1360795 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=O)=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].C1COCC1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[O:18][C:6]([C:5]3[CH:19]=[CH:20][C:2]([NH2:1])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=3)=[N:8][N:9]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 466515574-Chloro-benzoic acid N'-(4-amino-3-nitro-benzoyl)-hydrazide

Product 1

HCID 669656894-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 20 mL microwave vial was added 1.00 g (2.99 mmol) of 4-Chloro-benzoic acid N′-(4-amino-3-nitro-benzoyl)-hydrazide (A in Example 1-28), 12 mL of THF, and 1.9934 g (8.36 mmol) of burgess reagent. The suspension was placed in the microwave at 150° C. for 30 min. To the orange/yellow suspension was added 5 mL of MeOH and the precipitates were collected by filtration to yield the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.31 (d, J=8.97 Hz, 1H) 7.80 (d, J=8.59 Hz, 2H) 8.12-8.19 (m, 2.7H) 8.25 (d, J=8.59 Hz, 2H) 8.77 (d, J=2.02 Hz, 1H). MS (m/z) 317.0 M (+1), tR=1.33, Meth 10

Workup

  1. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-f29eeb39b5fb41f8a1f3edda6d7243a1
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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