Triethyl(methoxycarbonylsulfamoyl)aminium → 2-Neopentyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

HRID 715829Notes

Reaction equation

HRID 715829 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[CH2:3][C:4]([NH:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=O.C([N+](CC)(CC)S(NC(=O)OC)(=O)=O)C>O1CCCC1>[CH2:3]([C:4]1[O:18][C:8]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[N:7][N:6]=1)[C:2]([CH3:20])([CH3:19])[CH3:1]

Participants

4

Reactant 2

HCID 2724995Triethyl(methoxycarbonylsulfamoyl)aminiumHCID 4628581N'-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide

Product 1

HCID 867020152-Neopentyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N′-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide (0.556 g, 1.991 mmol) and methyl N-(triethylammoniumsulfonyl)carbamate (0.572 g, 2.389 mmol) in tetrahydrofuran (10 ml) was heated to 120° C. in a microwave (Biotage Initiator) for 45 minutes. The crude reaction mixture was concentrated and purified by normal phase chromatography to give the title compound.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-33d919d6e8434710aa3900b1dfceb2de
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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