Cyclohexanemethylamine → HCID 19071297, compound

HRID 1955643Notes

Reaction equation

HRID 1955643 reaction equation
[CH:1]1N=C[N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[S:7])[CH:2]=1.[CH:13]1([CH2:19]N)[CH2:18][CH2:17][CH2:16]CC1>C(Cl)(Cl)Cl>[CH:10]1([CH2:9][NH:8][C:6]([NH:3][CH2:2][CH:1]2[CH2:16][CH2:17][CH2:18][CH2:13][CH2:19]2)=[S:7])[CH2:19][CH2:13][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 19071297HCID 19071297, compoundYield 720.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of N,N'-thiocarbonyldiimidazole (Aldrich, 90%, 3.64 g, 18.4 mmol) in chloroform (20 mL) was added dropwise to a solution of cyclohexanemethylamine (Aldrich, 98%, 5.00 g, 4.33 mmol) in chloroform (10 mL). The reaction mixture was then stirred at 50° C. for 2 h, cooled to ambient temperature, and washed with hydrochloric acid (0.1N, 3×50 mL) and water (50 mL). The organic layer was dried (magnesium sulfate), and concentrated under vacuum to a yellow solid, which was recrystallized from ethanol. The mother liquor from this crystallization was concentrated, and the resulting solid was recrystallized from toluene. The two crops of crystals were combined and dried under vacuum to provide 1,3-bis(cyclohexylmethyl)thiourea as a pale yellow powder (4.19 g, 85%), m.p. 124°-125° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. temperaturecooled to ambient temperature
  2. washwashed with hydrochloric acid (0.1N, 3×50 mL) and water (50 mL)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated under vacuum to a yellow solid, which
  5. customwas recrystallized from ethanol
  6. customThe mother liquor from this crystallization
  7. concentrationwas concentrated
  8. customthe resulting solid was recrystallized from toluene
  9. customdried under vacuum

Sources & evidence

ORD record
ord-a3f2e4e63a0e4e2e869df542488a08cd
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

Loading…