Carbon Tetrachloride → HCID 21223284, compound

HRID 1939146Notes

Reaction equation

HRID 1939146 reaction equation
O[N:2]=[CH:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:20])([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)[CH3:11])[C:6](=[O:21])[C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>ClCCl>[C:3]([C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:20])([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)[CH3:11])[C:6](=[O:21])[C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[N:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86751703HCID 86751703, compound

Product 1

HCID 21223284HCID 21223284, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Hydroxyiminomethyl-3-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-one (Compound No. 135, 0.50 g), triphenylphosphine (0.33 g), carbon tetrachloride (0.19 g) and triethylamine (0.13 g) were mixed, and dichloromethane (5 ml) was added thereto. The mixture was refluxed for two and one-half hours. The reaction mixture was rinsed with water and dried with magnesium sulfate, then the solvent was removed by evaporation and the crude product was purified by silica gel chromatography to afford the captioned compound (0.39 g, yield 82%).

Workup

  1. temperatureThe mixture was refluxed for two and one-half hours
  2. washThe reaction mixture was rinsed with water
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-173bbc2ecda048e3ae0796ab27a54096
Source dataset
uspto-grants-1997_12
Patent number
US05696054

Reaction notes

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