Water → Benzamide, 2-amino-5-chloro-N-methyl-

HRID 2118022Notes

Reaction equation

HRID 2118022 reaction equation
[Cl:1][C:2]1[CH:13]=[C:6]2[C:7](OC(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH3:14][NH2:15].C(OCC)(=O)C.O>O1CCCC1>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=1[C:7]([NH:15][CH3:14])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8857Ethyl AcetateHCID 784805-Chloroisatoic anhydride

Product 1

HCID 209072Benzamide, 2-amino-5-chloro-N-methyl-Yield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloroisatoic anhydride (10.0 g, 51 mmol) in tetrahydrofuran (100 ml) at ambient temperature was added a 40% w/w aqueous solution of methylamine (19.80 g, 255 mmol) dropwise. The mixture was stirred at an ambient temperature for 1 hour. Ethyl acetate (100 ml) and water (100 ml) were added and the phases separated. The aqueous layer was back extracted with ethyl acetate (100 ml) and the combined organics were evaporated under reduced pressure to afford a white solid, which was recrystallised from toluene (60 ml) to afford the title compound as a white solid (8.15 g)

Workup

  1. customthe phases separated
  2. extractionThe aqueous layer was back extracted with ethyl acetate (100 ml)
  3. customthe combined organics were evaporated under reduced pressure
  4. customto afford a white solid, which
  5. customwas recrystallised from toluene (60 ml)

Sources & evidence

ORD record
ord-3371acea472c4b36a3f2980164e510d6
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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