4-Chlorophenyl Isocyanate → 3-Carbethoxy-4-(4-chlorophenylaminocarbonyl)thiomorpholine

HRID 27006

Reaction equation

HRID 27006 reaction equation
[C:1]([CH:6]1[CH2:11][S:10][CH2:9][CH2:8][NH:7]1)([O:3][CH2:4][CH3:5])=[O:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1>C(N(CC)CC)C>[C:1]([CH:6]1[CH2:11][S:10][CH2:9][CH2:8][N:7]1[C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)=[O:21])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 13604869Ethyl thiomorpholine-3-carboxylate

Product 1

HCID 233434093-Carbethoxy-4-(4-chlorophenylaminocarbonyl)thiomorpholineYield 30.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

Seven grams of 3-carbethoxythiomorpholine and 6.5 g of 4-chlorophenyl isocyanate were added to 60 ml of hexanes containing 10 drops of triethylamine as a catalyst. A mild exothermic reaction took place as the reactants mixed. After the mixture cooled to room temperature, the precipitate was collected by filtration and recrystallized from a mixture of methylene chloride and ether to give 4 g of 3-carbethoxy-4-(4-chlorophenylaminocarbonyl)thiomorpholine, mp 152.5°-154.5° C.

Workup

  1. customA mild exothermic reaction
  2. additionmixed
  3. filtrationthe precipitate was collected by filtration
  4. customrecrystallized from a mixture of methylene chloride and ether

Sources & evidence

ORD record
ord-9654ff91796547b1bc485f42a54b4c55
Source dataset
uspto-grants-1980_09
Patent number
US04220465

Linked notes

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