4-(Cyclohexylamino)-3-nitrobenzonitrile → HCID 178526500, compound

HRID 1788586Notes

Reaction equation

HRID 1788586 reaction equation
[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[N+:16]([O-:18])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Sn]([N:23]=[N+:24]=[N-:25])(C)(C)C>C1(C)C=CC=CC=1>[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]3[NH:25][N:24]=[N:23][N:13]=3)=[CH:10][C:9]=2[N+:16]([O-:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 29852004-(Cyclohexylamino)-3-nitrobenzonitrile2×HCID 5104973Azido(trimethyl)stannane

Product 1

HCID 178526500HCID 178526500, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.10 g (4.49 mmol) of 4-cyclohexylamino-3-nitrobenzonitrile, Compound 127, and 1.11 g (5.39 mmol) of Me3SnN3 in 50 mL toluene was refluxed overnight. The crystals were collected by filtration, washed with toluene, dried, and treated with 50 mL 4M HCl in dioxane for 4 h. The solids were collected by filtration, washed with dioxane, and dried yielding 1.14 g (88%) red solids. MS: 289.15 (M+H+).

Workup

  1. filtrationThe crystals were collected by filtration
  2. washwashed with toluene
  3. customdried
  4. additiontreated with 50 mL 4M HCl in dioxane for 4 h
  5. filtrationThe solids were collected by filtration
  6. washwashed with dioxane
  7. customdried

Sources & evidence

ORD record
ord-0095f0c8461a44d6ade5ffbb54532335
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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