Triethylamine → HCID 20439515, compound

HRID 1979599Notes

Reaction equation

HRID 1979599 reaction equation
[CH3:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:14].[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[N:4]=[C:3]1[O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 222232384-Methyl-1-(4-methylphenyl)-3-pyrazolidinone

Product 1

HCID 20439515HCID 20439515, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution under nitrogen of 4-methyl-1-p-tolyl-3-pyrazolidinone (19.0 g, 0.10 mole) and t-butyldimethylsilyl chloride (16.6 g, 0.11 mole) in 200 ml toluene, was added sequentially triethylamine (10.6 g, 0.11 mole), 1,8-diazabicyclo- [5.4.0]-undec-7-ene (0.1 g), and 4-(N,N-dimethylamino) pyridine (0.1 g). The mixture was refluxed for 16 hours, cooled to room temperature and filtered. The salts were washed with ether and the solvents of the combined filtrate were removed under reduced pressure. The resulting residue was treated with 200 ml adhydrous ether, filtered to remove salts, and dried over anhydrous magnesium sulfate. Removal of the solvent yielded 29.8 g (98% yield).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. filtrationfiltered
  3. washThe salts were washed with ether
  4. customthe solvents of the combined filtrate were removed under reduced pressure
  5. additionThe resulting residue was treated with 200 ml adhydrous ether
  6. filtrationfiltered
  7. customto remove salts
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customRemoval of the solvent
  10. customyielded 29.8 g (98% yield)

Sources & evidence

ORD record
ord-5a2ff95311d743dcb583243e6cc5af76
Source dataset
uspto-grants-1984_11
Patent number
US04481287

Reaction notes

Loading…