tert-Butyl carbazate → N'-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester

HRID 1931580Notes

Reaction equation

HRID 1931580 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18]>>[C:21]([O:20][C:16]([NH:17][N:18]=[C:12]1[CH2:13][CH2:14][CH:9]([C:7]2[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=2)[CH2:10][CH2:11]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 70091tert-Butyl carbazateHCID 579649554-(3-Isopropyl-1,2,4-oxadiazol-5-YL)cyclohexan-1-one2×

Product 1

HCID 66915389N'-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)cyclohexylidene]-hydrazinecarboxylic acid tert-butyl esterYield 77%

Procedure

A mixture of 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexanone (Intermediate 11; 1.6 g, 7.7 mmol) and tert-butyl carbazate (1.12 g, 8.5 mmol) in hexanes (3 mL) was heated at reflux for 3 h, then allowed to cool to room temperature and stand overnight. The white solid was filtered off, washed with hexanes and held under high vacuum to give N′-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester (1.9 g, 77%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.22 (d, 6H, J=6.9 Hz), 1.41 (s, 9H), 1.60-1.76 (m, 2H), 1.98-2.20 (m, 2H), 2.25-2.36 (m, 2H), 2.75-2.84 (m, 1H), 2.96-3.06 (m, 1H), 3.24-3.35 (m, 2H), 9.62 (br s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe white solid was filtered off
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-dbe407cb42a24913824560ceb3e41282
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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