N-bromobutanimide → HCID 19977110, compound

HRID 1450477Notes

Reaction equation

HRID 1450477 reaction equation
C[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=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][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19977111HCID 19977111, compound

Product 1

HCID 19977110HCID 19977110, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Following the procedure of Example 11, Step 6, 0.666 g (2.89 mmol) 3-methyl-5-(1-methyltetrazol-5-yl)benzo[b]thiophene was reacted with 0.515 g (2.89 mmol) of N-bromosuccinimide and 38.1 mg of benzoyl peroxide in 30 ml of carbon-tetrachloride. The reaction mixture was evaporated in vacuo and chromatographed on flash silica, eluting with 0-3% methanol/dichloromethane to give 0.532 g of crude 3-bromo-5-(1-methyltetrazol-5-yl) benzo[b]thiophene.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customchromatographed on flash silica
  3. washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-91cab664dc0e469a86fa68c39576ea01
Source dataset
uspto-grants-1997_02
Patent number
US05602162

Reaction notes

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