Triethylamine → HCID 54515720, compound

HRID 2119201Notes

Reaction equation

HRID 2119201 reaction equation
[C:1]([O:7][CH2:8][CH:9]=[CH2:10])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.C1(C)C=CC(S([N:27]=[N+:28]=[N-])(=O)=O)=CC=1>C(#N)C>[N+:27](=[CH:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])=[N-:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 70701Allyl acetoacetate

Product 1

HCID 54515720HCID 54515720, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of allyl acetoacetate (226.5 g, 1.594 mole) in 3 l acetonitrile and triethylamine (243.4 ml, 1.753 mole), there was added p-toluenesulfonyl azide (345.3 ml, 1.753 mole) over a 1 hour period while keeping the temperature at ~20° C. with a cooling bath. The reaction mixture became yellow. The reaction mixture was then stirred at room temperature under a nitrogen atmosphere for 18 hours. The mixture was concentrated on a rotary evaporator. The residue was dissolved in diethyl ether (2.6 l) and 1M aqueous KOH (800 ml). The organic phase was washed five times with 1M KOH (500 ml) and once with brine (400 ml). After drying over MgSO4 and concentration on a rotary evaporator (temp. ≤30° C.), there was obtained 260.2 g (97%) of the title product.

Workup

  1. customat ~20° C.
  2. concentrationThe mixture was concentrated on a rotary evaporator
  3. dissolutionThe residue was dissolved in diethyl ether (2.6 l)
  4. washThe organic phase was washed five times with 1M KOH (500 ml)
  5. dry with materialAfter drying over MgSO4 and concentration on a rotary evaporator (temp. ≤30° C.)

Sources & evidence

ORD record
ord-e51b85c7313a40e186061b10658dcad4
Source dataset
uspto-grants-1987_07
Patent number
US04683296

Reaction notes

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