2,4-Dichlorophenyl isocyanate → 1-(2,4-Dichloro-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-urea

HRID 966070Notes

Reaction equation

HRID 966070 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH2:14])[CH2:4][O:3]1.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[N:24]=[C:25]=[O:26]>CCCCC.ClCCl>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[NH:24][C:25]([NH:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:26]

Participants

5

Reactant 2

HCID 757892,4-Dichlorophenyl isocyanateHCID 7061833(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine

Product 1

HCID 104532731-(2,4-Dichloro-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-ureaYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

To a solution of 102 mg (0.49 mmol) of (4S,5S)-amine 1 in pentane (3 mL) was added a solution of 74 mg (0.39 mmol) of 2,4-dichlorophenyl isocyanate in dichloromethane (0.1 mL). A white precipitate was observed and collected via filtration. The crude solid was dissolved in dichloromethane (˜4 mL) and washed with 0.1 N HCl (˜4 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to yield 91 mg (59%) of the title compound.

Workup

  1. filtrationcollected via filtration
  2. dissolutionThe crude solid was dissolved in dichloromethane (˜4 mL)
  3. washwashed with 0.1 N HCl (˜4 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7e6d4d13642c497cb761ff3edbfb6c2e
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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