Azobisisobutyronitrile → HCID 70165804, compound

HRID 1250232Notes

Reaction equation

HRID 1250232 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[C:21]([O:28][CH3:29])[CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]2[CH3:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:38])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[C:21]([O:28][CH3:29])[CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]2[CH2:30][Br:38])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 45118278HCID 45118278, compound

Product 1

HCID 70165804HCID 70165804, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the product from Example 6, Step A (2380 mg, 5.73 mmol), NBS (1530 mg, 8.6 mmol), AIBN (94 mg, 0.57 mmol) in CCl4 (50 mL) was heated under reflux for 17 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum and the residue was purified by SiO2-gel chromatography using 30% EtOAc/hexanes to give the desired product (140 mg). API-MS: 492, 494 (M+1). 1H NMR (300 MHz, CDCl3): d 7.8 (d, 1 H), 7.4 (t, 1 H), 7.2 (d, 1 H), 4.5 (s, 2 H), 5.15 (t, 2 H), 4.0 (s, 3 H), 2.6 (m), 1.8-1.0 (m), 1.4 (s, 9 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum
  5. customthe residue was purified by SiO2-gel chromatography

Sources & evidence

ORD record
ord-17eef17e5be048f1be9821b402119be6
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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