3,4-Dichlorophenyl isocyanate → HCID 20431222, compound

HRID 2412854Notes

Reaction equation

HRID 2412854 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:23])[CH:12]([CH3:22])[CH2:13][N:14]2[CH2:19][CH:18]([CH3:20])[O:17][CH:16]([CH3:21])[CH2:15]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:31][C:32]1[CH:33]=[C:34]([N:39]=[C:40]=[O:41])[CH:35]=[CH:36][C:37]=1[Cl:38]>C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([O:23][C:40](=[O:41])[NH:39][C:34]2[CH:35]=[CH:36][C:37]([Cl:38])=[C:32]([Cl:31])[CH:33]=2)[CH:12]([CH3:22])[CH2:13][N:14]2[CH2:15][CH:16]([CH3:21])[O:17][CH:18]([CH3:20])[CH2:19]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 12768118HCID 12768118, compound

Product 1

HCID 20431222HCID 20431222, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

6.8 g (0.021 mole) of 1-(p-tert.-butyl-phenyl)-2-methyl-3-(2,6-dimethylmorpholin-4-yl)-1-propanol (obtained according to Example 2) and 0.6 mole of triethylamine were dissolved in 60 ml of acetonitrile, and a solution of 4.0 g of 3,4-dichlorophenyl isocyanate in 10 ml of acetonitrile was added dropwise at room temperature. The mixture was subsequently stirred under reflux for one hour, cooled and concentrated. The residue was taken up in ethyl acetate and the ethyl acetate was washed with water, dried over sodium sulphate and concentrated. 8.2 g (70% of theory) of 1-(p-tert.-butyl-phenyl)-1-(3,4-dichlorophenyl-carbamoyloxy)-2-methyl-3-(2,6-dimethylmorpholin-4-yl)-propane were obtained as a viscous oil.

Workup

  1. temperatureunder reflux for one hour
  2. temperaturecooled
  3. concentrationconcentrated
  4. washthe ethyl acetate was washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-028e9eef40fc4f0f87602627da98696b
Source dataset
uspto-grants-1985_01
Patent number
US04495184

Reaction notes

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