Dichloromethane → 4-Chloro-N-(5-isopropyl-2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 851980Notes

Reaction equation

HRID 851980 reaction equation
[N:1]([CH:4]1[CH2:10][CH:9]([CH:11]([CH3:13])[CH3:12])[CH2:8][CH2:7][NH:6][C:5]1=[O:14])=[N+]=[N-].CCN([CH:21]([CH3:23])[CH3:22])C(C)C.ClC1C=C[C:28]([CH2:29][S:30](Cl)(=[O:32])=[O:31])=[CH:27]C=1.C(Cl)[Cl:37]>C(O)C.O>[Cl:37][C:22]1[CH:21]=[CH:23][C:29]([S:30]([NH:1][CH:4]2[CH2:10][CH:9]([CH:11]([CH3:13])[CH3:12])[CH2:8][CH2:7][NH:6][C:5]2=[O:14])(=[O:32])=[O:31])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 860889383-Azido-5-isopropyl-azepan-2-one

Product 1

HCID 694892534-Chloro-N-(5-isopropyl-2-oxo-azepan-3-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

3-Azido-5-isopropyl-azepan-2-one (70 mg, 0.36 mmol) was dissolved in ethanol/water (2:1 v/v) and hydrogenated over 10% Pd-c (5 mg) for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was taken up in dry CH2Cl2 (5 ml) and Hünig's base (0.09 ml, 0.54 mmol) was added and this mixture was cooled (ice-bath) followed by the dropwise addition of 4-chlorobenzylsulfonyl chloride (90.3 mg, 0.43 mmol) in CH2Cl2 (0.5 ml). The reaction mixture was stirred at r.t. for 1 h and then diluted with CH2Cl2 and washed with NaHCO3 (1/2 sat., 3×), 5% KHSO4/10% K2SO4 (3×), water, brine, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product was purified over silica gel (ethyl acetate/n-heptane 1:2 to 1:1): white solid 0.08 g (75%); MS: m/e=343.0 (MH−)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. temperaturethis mixture was cooled (ice-bath)
  4. washwashed with NaHCO3 (1/2 sat., 3×), 5% KHSO4/10% K2SO4 (3×), water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe crude product was purified over silica gel (ethyl acetate/n-heptane 1:2 to 1:1)

Sources & evidence

ORD record
ord-ce7bc97c6b3a4f17b8d0e9ebef6f4b43
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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