Cyclohexyl isocyanide → HCID 178482102, compound

HRID 851756Notes

Reaction equation

HRID 851756 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[CH:13]1([N+:19]#[C-:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>Cl[Cu]>[CH:13]1([NH:19][CH:20]=[N:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[CH:10][NH:11][CH:12]=3)=[CH:6][CH:7]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 79129Cyclohexyl isocyanideHCID 178507418HCID 178507418, compound

Product 1

HCID 178482102HCID 178482102, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 1.59 gm of 4-(p-aminophenyl)-1-H-imidazole, 1.2 gm of cyclohexyl isonitrile, and 0.99 gm of CuCl was heated at 150° C. for three hours. The thick reaction mixture was extracted with methanol. The methanol solution, after treatment with charcoal, was evaporated to dryness and extracted with ethyl acetate and 10% hydrochloric acid. The acid solution was adjusted to pH 7.5 with 17% Na2CO3 and extracted with ethyl acetate. The organic solution was evaporated to dryness. The substance remaining after recrystallization from acetone comprised 0.25 gm of the desired product.

Workup

  1. extractionThe thick reaction mixture was extracted with methanol
  2. customThe methanol solution, after treatment with charcoal, was evaporated to dryness
  3. extractionextracted with ethyl acetate and 10% hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customThe organic solution was evaporated to dryness
  6. customafter recrystallization from acetone

Sources & evidence

ORD record
ord-fa3d940e6f6e4aed9d190c9d3b878397
Source dataset
uspto-grants-1983_05
Patent number
US04386099

Reaction notes

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