Triethylamine → 2-diazocyclohexane-1,3-dione

HRID 1179114Notes

Reaction equation

HRID 1179114 reaction equation
C(NC1C=CC(S([N:14]=[N+:15]=[N-])(=O)=O)=CC=1)(=O)C.C(N(CC)CC)C.[C:24]1(=[O:31])[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1>ClCCl>[N+:14](=[C:25]1[C:26](=[O:30])[CH2:27][CH2:28][CH2:29][C:24]1=[O:31])=[N-:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 110624492-diazocyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-acetamidobenzenesulphonylazide (25 g, 104 mmol) and triethylamine (36 ml, 250 mmol) in dichloromethane maintained at a temperature below 30° C. by external cooling is treated dropwise by a solution of cyclohexane-1,3-dione (13 g, 115 mmol) in 200 ml of dichloromethane. The reaction mixture is stirred for 75 minutes at ambient temperature then filtered on Celite. After concentration to approximately 300 ml, the filtrate is washed with water then dried over sodium sulphate. The brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure is similar to that obtained in Example 55.1, and is used as it is in the following stage.

Workup

  1. temperaturemaintained at a temperature below 30° C.
  2. temperatureby external cooling
  3. filtrationthen filtered on Celite
  4. concentrationAfter concentration to approximately 300 ml
  5. washthe filtrate is washed with water
  6. dry with materialthen dried over sodium sulphate
  7. customThe brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure
  8. customthat obtained in Example 55.1

Sources & evidence

ORD record
ord-00a017f2a18f4ac691b714af8fe33c32
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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