Azobisisobutyronitrile → HCID 59593469, compound

HRID 2261243Notes

Reaction equation

HRID 2261243 reaction equation
[CH:1]1([C:7]([C:15]2[O:16][C:17]([CH3:20])=[CH:18][N:19]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:21]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)([O-])O.[Na+]>ClCCCl>[Br:21][CH2:20][C:17]1[O:16][C:15]([C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])=[N:19][CH:18]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 59593472HCID 59593472, compound2×

Product 1

HCID 59593469HCID 59593469, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of cyclohexyl-(5-methyl-oxazol-2-yl)-phenyl-methanol (Intermediate 3) (3.0 g, 11.1 mmol) in 1,2-dichloroethane (22 mL) was treated with N-bromo-succinimide (2.16 g, 12.2 mmol) followed by 2,2′-azobis(2-methylpropionitrile) (0.18 g, 2.1 mmol). The mixture was heated to 80° C. for 2.5 h and then allowed to cool to RT. Satd. sodium hydrogen carbonate solution (aq.) was added and the phases were separated. The organic layer was washed with brine and the combined aqueous layers were extracted with DCM. The combined organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product as a brown oil. Purification was achieved via column chromatography eluting with 33-100% DCM/cyclohexane, followed by 25% EtOAc/DCM.

Workup

  1. temperatureto cool to RT
  2. customthe phases were separated
  3. washThe organic layer was washed with brine
  4. extractionthe combined aqueous layers were extracted with DCM
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-264e9b7322244fa5a868f95a34be97d9
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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