Azobisisobutyronitrile → HCID 24784534, compound

HRID 1436076Notes

Reaction equation

HRID 1436076 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][C:10]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[N:22])[CH:17]=3)[C:11]=2[N:12]=1.BrNC(=O)CCC(N)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:23])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][C:10]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[N:22])[CH:17]=3)[C:11]=2[N:12]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 9834204N-BromosuccinamideHCID 24784533HCID 24784533, compound

Product 1

HCID 24784534HCID 24784534, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-4,5-dihydronaphtho[1,2-d][1,3]thiazole-7-carbonitrile (0.65 g, 2.0 mmol), prepared in step 5 of Example 6, N-bromosuccinamide (0.39 g, 2.2 mmol) and a catalytic amount of 2,2′-azobis(2-methylproprionitrile) were stirred in carbontetrachloride (68 mL) at reflux for 4 h. The reaction was diluted with ethyl acetate and washed with 10% sodium thiosulfate. The layers were separated and the organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 0.64 g of crude product. Purification of the crude product on silica gel using a stepwise gradient of 6:1 to 1:1 hexane:ethyl acetate as the eluent gave 0.35 g of product that contained an impurity. Recrystallization from ethyl acetate afforded the title compound (0.02 g, 3%), mp>230° C.

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with 10% sodium thiosulfate
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 0.64 g of crude product
  8. customPurification of the crude product on silica gel using a stepwise gradient of 6:1 to 1:1 hexane

Sources & evidence

ORD record
ord-b10525d77d994e0d9d2c08d5103cd55e
Source dataset
uspto-grants-2009_11
Patent number
US07618989B2

Reaction notes

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