N-bromobutanimide → HCID 19977128, compound

HRID 2399710Notes

Reaction equation

HRID 2399710 reaction equation
[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:12]=[N:13][N:14]([CH3:16])[N:15]=3)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:12]=[N:13][N:14]([CH3:16])[N:15]=3)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19977136HCID 19977136, compound

Product 1

HCID 19977128HCID 19977128, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing mixture of 3-methyl-5-(2-methyltetrazol-5-yl)benzo[b]thiophene (0.162 g, 0.703 mmol) and benzoyl peroxide (10.6 mg) in carbon tetrachloride (10 ml) irradiated with two desk lamps (2×60 W) was added N-bromosuccinimide (0.126 g, 0.707 mmol) in small portions. After the addition was complete the mixture was heated at reflux for a further 90 min, then filtered and the filtrate was evaporated in vacuo to leave an oil/solid mixture. Chromatography on flash silica, eluting with dichloromethane gave 0.161 g of crude 3-bromomethyl-5-(2-methyltetrazol-5-yl)benzo[b]thiophene as a colourless oil.

Workup

  1. customirradiated with two desk lamps (2×60 W)
  2. additionAfter the addition
  3. temperaturewas heated
  4. temperatureat reflux for a further 90 min
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customto leave an oil/solid mixture
  8. washChromatography on flash silica, eluting with dichloromethane

Sources & evidence

ORD record
ord-d2562a3f3df34eb3b52bbbca14bda813
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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