N-Methylcyclohexylamine → 1,3-dicyclohexyl-1-methylurea

HRID 540969Notes

Reaction equation

HRID 540969 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[CH3:18]CCCCC>>[CH:1]1([N:7]([CH3:18])[C:8]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 8058HexaneHCID 18502Cyclohexyl isocyanate

Product 1

HCID 8536641,3-dicyclohexyl-1-methylurea

Procedure

18.38 g of cyclohexyl isocyanate (0.147 mol) are added dropwise to a solution of 19.12 g of N-methyl-N-cyclohexylamine (0.169 mol) in 160 ml of hexane and then the cloudy mixture is refluxed for 2 h and then evaporated to dryness, to give 35 g of crude N,N′-dicyclohexyl-N-methylurea. 12 g of POCl3 (78 mmol) is added, over 1 h, to a suspension of 17 g of said N,N′-dicyclohexyl-N-methylurea (71.33 mmol) in 65 ml of toluene, and then, after a few hours at 20° C., 15.5 g of N-butyl-N-methylamine (0.178 mmol) are added over 2 h, and then, after a further 2 h at 20° C., 50 ml of water are added. 49 g of 35% sodium hydroxide are then added while cooling, and the two-phase medium is then extracted with diisopropyl ether. After drying and evaporation to dryness, the oil obtained, 26.5 g, is distilled at 180° C. under 1 mbar, to give 21.25 g of the expected guanidine (yield 97%).

Workup

  1. temperaturethe cloudy mixture is refluxed for 2 h
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-719ad6c28c074ff88d29f7bd651f8438
Source dataset
uspto-grants-2014_10
Patent number
US08871889B2

Reaction notes

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