Morpholine, 4-(1-cyclohexen-1-yl)- → HCID 12832956, compound

HRID 647401Notes

Reaction equation

HRID 647401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[C:4]([F:11])[CH:3]=1.[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:23]2[CH2:22][CH2:21][CH2:20][CH:19]=[C:18]2[N:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)=[S:10])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 27575844-Chloro-2-fluorophenyl isothiocyanate

Product 1

HCID 12832956HCID 12832956, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 400 ml of chloroform was dissolved 78.9 g of 4-chloro-2-fluorophenyl isothiocyanate, and 68.6 g of 1-morpholino-1-cyclohexene was added dropwise to the solution with stirring over a 10-minute period. After stirring was continued at room temperature for 10 hours, the reaction mixture was concentrated under reduced pressure, and the residue was treated with a small amount of cold ethanol. The resulting crystals were collected by filtration, and there was obtained 127.9 g (yield of 86%) of the subject compound, m.p. 86°-88° C.

Workup

  1. additionwas added dropwise to the solution
  2. stirringAfter stirring
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was treated with a small amount of cold ethanol
  5. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-f9bbbfb989f3425b8a35eb39c23bad35
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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