Cyclohexyl isocyanate → HCID 178511685, compound

HRID 522197Notes

Reaction equation

HRID 522197 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.[CH:16]1([N:22]=[C:23]=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1COCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:23]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:24])[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 8028TetrahydrofuranSolvent

Procedure

Trans-1,4-diaminocyclohexane (6.15 g, 0.054 mmol) was added in a flame dried Schlenk flask and dissolved in THF (500 mL) under argon atmosphere. The solution was cooled to −40° C. in a cooling bath (isopropyl alcohol/dry ice) and cyclohexyl isocyanate (6.75 g, 0.054 mmol), diluted in THF (100 mL), was added slowly under heavy stirring. The reaction mixture was stirred for 12 h at room temperature. The precipitated white solid was filtered off, 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 the trans-1-(4-aminocyclohexyl)-3-cyclohexylurea precipitated as a white solid.

Workup

  1. customdried Schlenk flask
  2. dissolutiondissolved in THF (500 mL) under argon atmosphere
  3. additionwas added slowly under heavy stirring
  4. filtrationThe precipitated white solid was filtered off
  5. filtrationThe emerging clear solution was again filtrated
  6. customprecipitated as a white solid

Sources & evidence

ORD record
ord-a95b58c055ea40ed86249adeedd06b39
Source dataset
uspto-grants-2016_05
Patent number
US09328219B2

Reaction notes

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