p-Anisoyl chloride → HCID 59737421, compound

HRID 1907710Notes

Reaction equation

HRID 1907710 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:22][CH:23]=[CH:24][CH:25]=2)=[CH:17][C:16]=1[NH2:26])([O-:14])=[O:13].C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:26][C:16]2[CH:17]=[C:18]([C:21]3[NH:22][CH:23]=[CH:24][CH:25]=3)[CH:19]=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 516892Sodium BicarbonateHCID 59737447HCID 59737447, compound

Product 1

HCID 59737421HCID 59737421, compoundYield 101.1%

Reagents, catalysts & solvents 3

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

Procedure

A solution of 4-methoxybenzoyl chloride (145, 0.175 g, 1.0 mmol), aniline 144 (79.2 mg, 0.39 mmol) and 4-(dimethylamino)pyridine (catalytic amount) was stirred at room temperature for 24 h. The reaction mixture was diluted with DCM, treated with saturated NaHCO3, stirred for 3 h and diluted with AcOEt. Organic phase was collected, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to provide compound 146 (0.133 g, 100% yield).

Workup

  1. customOrganic phase was collected
  2. washwashed with saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2b2b166747049a8ba2b8f43fbf58656
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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