Triethylamine → HCID 11040878, compound

HRID 1179111Notes

Reaction equation

HRID 1179111 reaction equation
C(N(CC)CC)C.C(NC1C=CC(S([N:21]=[N+:22]=[N-])(=O)=O)=CC=1)(=O)C.[CH3:24][CH:25]1[CH2:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[CH2:26]1>ClCCl>[N+:21](=[C:28]1[C:29](=[O:31])[CH2:30][CH:25]([CH3:24])[CH2:26][C:27]1=[O:32])=[N-:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4580955-Methylcyclohexane-1,3-dioneHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 11040878HCID 11040878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.25 ml (87.2 mmol; 2.2 eq.) of triethylamine and 8.57 g (35.67 mmol; 0.9 eq.) of 4-acetamidobenzenesulphonylazide are added to a solution of 5 g (39.6 mmol) of 5-methylcyclohexane-1,3-dione in 100 ml of dichloromethane. The reaction mixture is stirred for 75 minutes at ambient temperature, then cooled down to 0° C. and filtered on a silica bed. After concentration under reduced pressure, the solution is washed with 3 times 50 ml of water. The organic phases are combined, dried over sodium sulphate and concentrated. The resulting solid is taken up in ethyl ether followed by filtering and drying under reduced pressure. It is used in the following stage without other purification.

Workup

  1. temperaturecooled down to 0° C.
  2. filtrationfiltered on a silica bed
  3. concentrationAfter concentration under reduced pressure
  4. washthe solution is washed with 3 times 50 ml of water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. filtrationby filtering
  8. customdrying under reduced pressure
  9. customIt is used in the following stage without other purification

Sources & evidence

ORD record
ord-5d45e5724e824f6f87ecc4430551caac
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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