Triethylamine → Ethyl 4-(4-bromo-phenylsulphanyl)-5-oxo-azepan-1-carboxylate

HRID 1916659Notes

Reaction equation

HRID 1916659 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[CH:10]1[C:16](=[O:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:10]2[C:16](=[O:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660494-BromothiophenolHCID 69077672Ethyl 4-bromo-5-oxo-azepan-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

60.5 g (320 mmol) 4-bromothiophenol in 300 mL chloroform are added to a solution of 84.5 g (320 mmol) ethyl 4-bromo-5-oxo-azepan-1-carboxylate and 32.4 g (320 mmol) triethylamine in 80 mL chloroform over 45 min, so that the internal temperature does not exceed 40° C. The reaction solution is stirred for 1.5 h at RT. The reaction mixture is washed twice with dilute ammonia solution and twice with water. 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. customdoes not exceed 40° C
  2. washThe reaction mixture is washed twice with dilute ammonia solution and twice with water
  3. dry with materialThe organic phase is dried over Na2SO4 and K2CO3
  4. customThe purification

Sources & evidence

ORD record
ord-4ec93c4ee9ec4c0fb81cb1ce5a720628
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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