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 1916660Notes

Reaction equation

HRID 1916660 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-f88312fd1c9b41ddb9c8f10ce1e5bf40
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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