Azobisisobutyronitrile → HCID 67721486, compound

HRID 1449644Notes

Reaction equation

HRID 1449644 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:12][C@@H:11]1[O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]/[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:23][Si:24]([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:25])[CH3:26])[CH2:12][C@@H:11]1[O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 67720997HCID 67720997, compound

Product 1

HCID 67721486HCID 67721486, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The compound 116 obtained above (7.27 g, 12.5 mmole) was dissolved in benzene (40 ml), and 5-mercapto-1-methyltetrazole disulfide (2.88 g, 12.5 mmole) and α,α'-azobis-isobutyronitrile (205 mg, 1.25 mmole) were added thereto, and the mixture was refluxed with stirring for 19 hours. Then, the reaction mixture was treated following the procedure similar to that of Example 41, to yield a residue. The residue was chromatographed over silica gel (330 g), eluting with ethyl acetate: n-hexane (1:50), to yield 5.34 g of a mixture of geometrical isomers with respect to the double bond. The material was further chromatographed over 10% silver nitrate--silica gel (500 g), eluting with ether-n-hexane (1:50), to yield 3.64 g of the title compound 117 (yield 50%).

Workup

  1. temperaturethe mixture was refluxed
  2. additionThen, the reaction mixture was treated
  3. customto yield a residue
  4. customThe residue was chromatographed over silica gel (330 g)
  5. washeluting with ethyl acetate: n-hexane (1:50)

Sources & evidence

ORD record
ord-7b3e50d6cf2143d492c857ec0b8479cf
Source dataset
uspto-grants-1997_02
Patent number
US05599837

Reaction notes

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