tert-Butyl isocyanate → HCID 86696625, compound

HRID 522196Notes

Reaction equation

HRID 522196 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[CH2:11][CH2:10]1>CN1CCCC1=O>[C:1]([NH:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:17])[NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 178511685HCID 178511685, compound

Product 1

HCID 86696625HCID 86696625, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of tert-butylisocyanate (1.17 g, 0.012 mol) in dry N-methyl-2-pyrrolidone (NMP) (50 mL) was added slowly to a solution of trans-1-(4-aminocyclohexyl)-3-cyclohexylurea (2.83 g, 0.012 mol) in dry NMP (100 mL) under inert atmosphere. The resulting mixture was heated to 70° C. and stirred for 24 h. The solution was precipitated in 1 M HCl and filtered off. The resulting white solid was washed with THF, recrystallized from DMF and dried under high vacuum.

Workup

  1. customThe solution was precipitated in 1 M HCl
  2. filtrationfiltered off
  3. washThe resulting white solid was washed with THF
  4. customrecrystallized from DMF
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e350795ef55f4263a8b70a4f92b4140b
Source dataset
uspto-grants-2016_05
Patent number
US09328219B2

Reaction notes

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