Cyclohexylamine → HCID 178471915, compound

HRID 963401Notes

Reaction equation

HRID 963401 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][NH:27][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 53916769Ethyl 2-(2-chloro-4-iodo-benzoyl)-3-ethoxy-acrylate

Product 1

HCID 178471915HCID 178471915, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mf) A solution of 31.18 g of ethyl 2-(2-chloro-4-iodo-benzoyl)-3-ethoxy-acrylate in 500 ml of methylene chloride is treated dropwise with 7.95 g of cyclohexylamine while cooling with ice and stirring. After 6 hrs. at room temperature the reaction mixture is concentrated and, for crystallization, the residue is stirred with 200 ml of hexane. The precipitate is filtered off under suction, washed with 100 ml of hexane and dried. 19.2 g (55%) of ethyl 2-(2-chloro-4-iodo-benzoyl)-3-cyclohexylamino-acrylate are obtained as a colourless solid. M.p. 154°-156° C.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationat room temperature the reaction mixture is concentrated and, for crystallization
  3. stirringthe residue is stirred with 200 ml of hexane
  4. filtrationThe precipitate is filtered off under suction
  5. washwashed with 100 ml of hexane
  6. customdried

Sources & evidence

ORD record
ord-274eff2ed84a44fe97f498e076a1e225
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…