Cyclohexyl isocyanate → HCID 178511685, compound

HRID 522195Notes

Reaction equation

HRID 522195 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.C(O)(C)C.C(=O)=O.[N:16]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[C:17]=[O:18]>C1COCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:17]([NH:16][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 86586944Isopropanol carbon dioxideHCID 178511674HCID 178511674, compound

Product 1

HCID 178511685HCID 178511685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-1,4-diaminocyclohexane (6.15 g, 0.054 mol) in dry THF (500 mL) was cooled to −40° C. in a cooling bath (isopropyl alcohol/dry ice) under inert atmosphere. Isocyanatocyclohexane (6.75 g, 0.054 mol) in dry THF (100 mL) was added slowly under heavy stirring. The resulting mixture was stirred for another 24 h at room temperature. The precipitating white solid was filtrated, suspended in water and acidified to pH 2 (HCl). The emerging clear solution was again filtrated and the filtrate was brought to pH 8 (NaOH) whereupon trans-1-(4-aminocyclohexyl)-3-cyclohexylurea precipitated as a white solid.

Workup

  1. filtrationThe precipitating white solid was filtrated
  2. filtrationThe emerging clear solution was again filtrated
  3. customprecipitated as a white solid

Sources & evidence

ORD record
ord-07c064644ac14c8fa728a550e2ed1483
Source dataset
uspto-grants-2016_05
Patent number
US09328219B2

Reaction notes

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