Potassium Hydroxide → 3-bromo-6,7,8,9-tetrahydro-5H-10-thia-7-aza-benzo[a]azulene

HRID 1916661Notes

Reaction equation

HRID 1916661 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[S:16][C:15]3[CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11][CH2:10][C:9]=3[C:8]=2[CH:22]=1>CCO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[S:16][C:15]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10][C:9]=3[C:8]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69079455Ethyl 3-bromo-5,6,8,9-tetrahydro-10-thia-7-aza-benzo[a]azulen-7-carboxylate

Product 1

HCID 673642873-bromo-6,7,8,9-tetrahydro-5H-10-thia-7-aza-benzo[a]azulene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30.0 g (53.5 mmol) KOH in 700 mL EtOH are added to a solution of 19.0 g (53.5 mmol) ethyl 3-bromo-5,6,8,9-tetrahydro-10-thia-7-aza-benzo[a]azulen-7-carboxylate. EtOH is distilled off at normal pressure and the residue is taken up in water. The solution is acidified with HCl. Then it is made basic with NaOH and the aqueous phase is extracted four times with chloroform. The organic phase is dried over Na2SO4 and K2CO3 and the solvent is eliminated i.vac. The purification is carried out by repeated column chromatography on silica gel.

Workup

  1. distillationEtOH is distilled off at normal pressure
  2. extractionthe aqueous phase is extracted four times with chloroform
  3. dry with materialThe organic phase is dried over Na2SO4 and K2CO3
  4. customThe purification

Sources & evidence

ORD record
ord-9c1ca038d9754db294e1a90cb777c17b
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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