Acetyl chloride → N-(4-(2-cyano-3-nitrophenoxy)butyl)acetamide

HRID 711859Notes

Reaction equation

HRID 711859 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:8]=1[C:9]#[N:10].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>CN(C1C=CN=CC=1)C.ClCCl.CCOC(C)=O>[C:9]([C:8]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=[CH:14][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:25](=[O:27])[CH3:26])#[N:10]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66747054HCID 66747054, compound

Product 1

HCID 66747313N-(4-(2-cyano-3-nitrophenoxy)butyl)acetamideYield 57%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-aminobutoxy)-6-nitrobenzonitrile (Example 234d) (235 mg, 1.0 mmol), triethylamine (3 equiv.), and DMAP (0.1 equiv.) in dry dichloromethane (20 mL) was added dropwise acetyl chloride (1.5 equiv.) at 0° C. under nitrogen. The reaction mixture was then stirred at 0° C.—RT overnight. The reaction was diluted with EtOAc, washed with brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexanes to give the title compound (158 mg, 57%). MS 278 (MH+).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-7ba497f7d2994cdca2da9e4569c01913
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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