Ethyl 4-(4-bromo-phenylsulphanyl)-5-oxo-azepan-1-carboxylate → Ethyl 3-bromo-5,6,8,9-tetrahydro-10-thia-7-aza-benzo[a]azulen-7-carboxylate

HRID 271695Notes

Reaction equation

HRID 271695 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[C:15](=O)[CH2:14][CH2:13][N:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][C:9]3[CH2:10][CH2:11][N:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:14][C:15]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 69076506Ethyl 4-(4-bromo-phenylsulphanyl)-5-oxo-azepan-1-carboxylate

Product 1

HCID 69079455Ethyl 3-bromo-5,6,8,9-tetrahydro-10-thia-7-aza-benzo[a]azulen-7-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 44.3 g (119 mmol) ethyl 4-(4-bromo-phenylsulphanyl)-5-oxo-azepan-1-carboxylate in 443 g polyphosphoric acid is heated to 80° C. for 45 min and then diluted with 1000 mL water. The aqueous phase is extracted three times with chloroform. The organic phase is washed with water, dried over Na2SO4 and the solvent is eliminated i.vac. The purification is carried out by repeated column chromatography on silica gel (chloroform/EtOAc 19:1) and by recrystallisation from MeOH/acetone.

Workup

  1. extractionThe aqueous phase is extracted three times with chloroform
  2. washThe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. customThe purification
  5. customby recrystallisation from MeOH/acetone

Sources & evidence

ORD record
ord-fa318e5b87184f17936227f65864ce26
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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