Methyl N-(triethylammoniosulfonyl)carbamate → 2-(4-Bromo-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazole

HRID 2035679Notes

Reaction equation

HRID 2035679 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[O:14][CH3:15])(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.[Cl-].[Na+].O>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[O:16][C:1]([CH3:2])=[N:4][N:5]=2)=[C:8]([O:14][CH3:15])[CH:9]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66684712N'-acetyl-4-bromo-2-methoxybenzohydrazide

Product 1

HCID 597999112-(4-Bromo-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazoleYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

N′-Acetyl-4-bromo-2-methoxybenzohydrazide (720 mg, 2.51 mmol) and Burgess' Reagent (896 mg, 3.76 mmol) were dissolved in 10 ml of THF and stirred in the microwave at 120° C. for 30 minutes. The reaction was diluted with brine and extracted three times with EtOAc. Organics were combined, dried over sodium sulfate, and concentrated under reduced pressure to a yellow oil. Chromatography on silica gel (0-50% EtOAc/DCM) gave a yellow solid (465 mg, 1.73 mmol, 69%).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure to a yellow oil

Sources & evidence

ORD record
ord-6678369d78b14df9adbdb9cef8d36da5
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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