4-Aminobenzonitrile → 4-(3-Oxo-4-morpholinyl)benzonitrile

HRID 2246808Notes

Reaction equation

HRID 2246808 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl[C:11]1(Cl)[CH2:16][O:15][CH2:14][CH2:13][O:12]1>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:1]2[CH2:14][CH2:13][O:12][CH2:11][C:16]2=[O:15])=[CH:3][CH:4]=1)#[N:7]

Participants

3

Reactant 2

HCID 133964-AminobenzonitrileHCID 124243252,2-Dichloro-1,4-dioxane

Product 1

HCID 684509884-(3-Oxo-4-morpholinyl)benzonitrile

Conditions

Temperature
80 °C

Procedure

A mixture of 959 mg (8.12 mmol) of 4-aminobenzonitrile and 1.12 g of a mixture of 2-chlorodioxene and 2,2-dichlorodioxane (molar ratio 89:11) is heated at 80° C. with stirring for 18 hours. On cooling to room temperature, the product crystallises: 1.9 g of 2-(2-chloroethoxy)-N-(4-cyanophenyl)acetamide as yellowish crystals. 1H-NMR (d 6-DMSO): δ=3.82 (m; 4H), 4.19 (s; 2H), 7.78 (d, J=8 Hz, 2H), 7.85 (d, J=8 Hz, 2H), 10.22 (s, 1H).

Workup

  1. temperatureOn cooling to room temperature
  2. customthe product crystallises

Sources & evidence

ORD record
ord-9b00de00eb4341d0ae3d7d4aed852ca2
Source dataset
uspto-grants-2010_03
Patent number
US07687624B2

Reaction notes

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