N,N-Dimethylaniline → HCID 56971686, compound

HRID 2077051Notes

Reaction equation

HRID 2077051 reaction equation
[CH2:1]([C:8]1[NH:9][C:10](=O)[C:11]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13][C:12]=2[N:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:41]>C(#N)C>[CH2:1]([C:8]1[N:9]=[C:10]([Cl:41])[C:11]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13][C:12]=2[N:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 136058083HCID 136058083, compound

Product 1

HCID 56971686HCID 56971686, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of the product from step A (4 g, 10 mmol) in acetonitrile (100 ml) was added N,N-dimethylaniline (1.4 ml, 11.3 mmol), followed by careful addition of POCl3 (9.6 ml, 100 mmol). The resulting brown solution was heated at 80° C. for 4 h. The reaction mixture was concentrated in vacuo, azeotroped with PhMe (×2) and DCM. The residue was partitioned between 2 N HCl and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo to yield 3.5 g (84%) of title compound as brown oil, which solidified on standing.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with PhMe (×2) and DCM
  3. customThe residue was partitioned between 2 N HCl and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4e5ae79284243f4b28acb85d2796fd3
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

Loading…