Azobisisobutyronitrile → HCID 67094164, compound

HRID 1881229Notes

Reaction equation

HRID 1881229 reaction equation
[CH3:1][O:2][C:3]1[C:20]([O:21][CH3:22])=[CH:19][C:6]2[S:7][C:8]([C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])=[C:9]([CH3:10])[C:5]=2[CH:4]=1.[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:10][C:9]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:20]([O:21][CH3:22])=[CH:19][C:6]=2[S:7][C:8]=1[C:11]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67094298HCID 67094298, compound

Product 1

HCID 67094164HCID 67094164, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(5,6-Dimethoxy-3-methylbenzo[b]thiophen-2-yl)morpholin-4-yl-methanone (2.0 g) from Example 20, N-bromosuccinimide (1.18 g) and 2,2′-azobis(2-methylpropionitrile) (40 mg) in carbon tetrachloride (6 ml) was refluxed under argon for 4 hours. The mixture was cooled and filtered and the filtrate evaporated to dryness. The product was a mixture of (4-bromo-5,6-dimethoxy-3-methyl-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone and (3-bromomethyl-5,6-dimethoxy-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone. The compounds were separated by flash chromatography using ethyl acetate/heptane (1:4) as an eluent.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. additiona mixture of (4-bromo-5,6-dimethoxy-3-methyl-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone and (3-bromomethyl-5,6-dimethoxy-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone
  5. customThe compounds were separated by flash chromatography

Sources & evidence

ORD record
ord-b3c9da6b876544f99525f24585b1c5c7
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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