N,N-Diethylaniline → HCID 13960862, compound

HRID 2119167Notes

Reaction equation

HRID 2119167 reaction equation
[CH2:1]([O:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:2][CH3:3].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16].C(N(CC)C1C=CC=CC=1)C.[H-].[Na+].[CH:35]([O:38][C:39]([C:41]1[C:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[N+:55]([O-:57])=[O:56])=[N:43][CH:44]([CH3:48])[NH:45][C:46]=1[CH3:47])=[O:40])([CH3:37])[CH3:36]>C1COCC1.CCCCCC>[CH:35]([O:38][C:39]([C:41]1[CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[N+:55]([O-:57])=[O:56])[N:43]([C:15]([O:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:13])=[CH:7][CH:8]=2)=[O:16])[C:44]([CH3:48])=[N:45][C:46]=1[CH3:47])=[O:40])([CH3:36])[CH3:37]

Participants

8

Reactant 5

HCID 7061N,N-DiethylanilineHCID 7175PropylparabenHCID 10426DiphosgeneHCID 24758Sodium hydrideHCID 20191099HCID 20191099, compound

Product 1

HCID 13960862HCID 13960862, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent5×HCID 8058HexaneSolvent

Procedure

A solution of 250 mg (1.35 millimole) of n-propyl-p-hydroxybenzoate in 7 ml of THF was added to a solution of 0.12 ml (1.00 millimole) of trichloromethyl chloroformate in 2 ml of THF and then a solution of 0.25 ml (1.57 millimole) of N,N-diethylaniline in 6 ml of THF was added dropwise. The reaction mixture was stirred for 1.5 hrs at room temperature. Independently, 0.30 g (6.25 millimole) of sodium hydride washed with hexane was suspended in 5 ml of THF and a solution of 200 mg (0.63 millimole) of 5-isopropyloxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-dihydropyrimidine in 5 ml os THF was added dropwise and stirred for 40 minutes at room temperature. And to this mixture the above reaction mixture was added and stirred for 30 minutes. Ice water was added and the mixture was extracted three times with ether. The organic layer was washed twice with water, dried over magnesium sulfate (dehydrating agent) and concentrated under reduced pressure. The residue was purified on silica gel by column chromatography (silica gel 30 g, eluant:benzene/ethyl acetate 9:1) to obtain 117 mg (35% yield) of tilte compound.

Workup

  1. stirringstirred for 40 minutes at room temperature
  2. additionAnd to this mixture the above reaction mixture was added
  3. stirringstirred for 30 minutes
  4. extractionthe mixture was extracted three times with ether
  5. washThe organic layer was washed twice with water
  6. dry with materialdried over magnesium sulfate (dehydrating agent)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on silica gel by column chromatography (silica gel 30 g, eluant:benzene/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-c5be33abbc5f4bb19e953eb2e087e38c
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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