Dichloromethane → 3-Azido-5-isopropyl-azepan-2-one

HRID 851979Notes

Reaction equation

HRID 851979 reaction equation
Cl[CH:2]1[CH2:8][CH:7]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:5][NH:4][C:3]1=[O:12].[N-:13]=[N+:14]=[N-:15].[Na+].C(Cl)Cl>CS(C)=O.O>[N:13]([CH:2]1[CH2:8][CH:7]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:5][NH:4][C:3]1=[O:12])=[N+:14]=[N-:15]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 694913233-Chloro-5-isopropyl-azepan-2-one

Product 1

HCID 860889383-Azido-5-isopropyl-azepan-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3-Chloro-5-isopropyl-azepan-2-one (3.4 g, 18 mmol) and sodium azide (3.51 g, 53.9 mmol) were reacted in dry dimethyl sulfoxide (50 ml) overnight at 80° C. under an argon atmosphere. The reaction mixture was allowed to cool to r.t. diluted with water (200 ml) and extrated with CH2Cl2 (4×). The combined organic fractions were washed with water (3×), brine and dried (MgSO4) filtered and evaporated under reduced pressure. The crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 1:2): yellow oil 2.6 g (70%); MS: m/e=197.4 (MH+)

Workup

  1. washThe combined organic fractions were washed with water (3×), brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 1:2)

Sources & evidence

ORD record
ord-5878004b8cc6455e8d7866e4885c3d29
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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