Ethanol → 2-Amino-N-[4-(2-chloro-ethoxy)-phenyl]-4-methoxy-benzamide

HRID 617122

Reaction equation

HRID 617122 reaction equation
CO[C:3]1C=C[C:6]2[C:9]([NH:11][C:12]([O:14][C:5]=2[CH:4]=1)=O)=O.[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.[CH2:26]([OH:28])[CH3:27]>CN(C)C1C=CN=CC=1>[NH2:11][C:9]1[CH:6]=[C:5]([O:14][CH3:12])[CH:4]=[CH:3][C:27]=1[C:26]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([O:18][CH2:17][CH2:16][Cl:15])=[CH:20][CH:21]=1)=[O:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 1196994-(2-Chloroethoxy)anilineHCID 218886767-Methoxy-1,3-benzoxazine-2,4-dione

Product 1

HCID 218510862-Amino-N-[4-(2-chloro-ethoxy)-phenyl]-4-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 11.11 g (0.0575 mol) of 7-methoxyisatoic anhydride in 300 mL of ethanol was added a catalytic amount of 4-dimethylaminopyridine and 144 mL of a 1M solution containing 24.7 g (0.144 mol) of 4-(2-chloroethoxy)-aniline. The reaction mixture was sired and heated under reflux for 3 hours. One half of the solvent was evaporated in a rotary evaporator. The reaction mixture was then cooled on ice. The precipitate that formed was collected by vacuum filtration and amounted to 16.4 g. An analytical sample (mp 167-168° C.) was obtained by recrystallization from ethanol.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customOne half of the solvent was evaporated in a rotary evaporator
  4. temperatureThe reaction mixture was then cooled on ice
  5. customThe precipitate that formed
  6. filtrationwas collected by vacuum filtration
  7. customAn analytical sample (mp 167-168° C.) was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-ad2ed429e08b477185993d2589fe700d
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Linked notes

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