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

HRID 1894909Notes

Reaction equation

HRID 1894909 reaction equation
C[NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:9]1([N:15]=[C:16]=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:18]CCCCC>>[CH:9]1([N:15]([CH3:18])[C:16]([NH:2][CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 8058HexaneHCID 18502Cyclohexyl isocyanate

Product 1

HCID 8536641,3-dicyclohexyl-1-methylurea

Procedure

A solution of 19.12 g of N-methyl-N-cyclohexylamine (0.169 mol) in 160 ml of hexane is admixed dropwise with 18.38 g of cyclohexyl isocyanate (0.147 mol) and then the cloudy mixture is heated at reflux for 2 hours, then evaporated to dryness to give 35 g of crude N,N′-dicyclohexyl-N-methylurea. A suspension of 17 g of this crude product (71.33 mmol) in 65 ml of dry toluene is admixed with 12 g of POCl3 (78 mmol) over 1 hour, and then, after a number of hours at 20° C., 15.5 g of N-butyl-N-methylamine (0.178 mmol) are added over 2 hours, and then, after a further 2 hours at 20° C., 50 ml of water are added. 49 g of 35% sodium hydroxide solution are then added while cooling, after which the two-phase mixture is extracted with diisopropyl ether. Following 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 (97% yield).

Workup

  1. temperaturethe cloudy mixture is heated
  2. temperatureat reflux for 2 hours
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-d11617548b1a4e45add6ebd1f8082f41
Source dataset
uspto-grants-2013_08
Patent number
US08513370B2

Reaction notes

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