Dimethylamine → 2-Amino-5-bromo-N,N-dimethylbenzamide

HRID 2388968Notes

Reaction equation

HRID 2388968 reaction equation
[Br: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][NH:15][CH3:16]>CN(C1C=CN=CC=1)C>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=1[C:7]([N:15]([CH3:16])[CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 509995122-Amino-5-bromo-N,N-dimethylbenzamideYield 106.1%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Into an 15 mL high pressure glass vial (with Teflon screw cap) were added 5-bromoisatoic anhydride (0.401 g, 1.66 mmol), DMAP (20 mg, 0.16 mmol), and dimethylamine (2 M in THF; 5.0 mL, 10.0 mmol). The vial was sealed and placed in an oil bath at 70° C. for 8 h after which it was concentrated under vacuum. The crude product was dissolved in Ethyl acetate and washed 2× with water followed by brine. The organic phase was dried (Sodium sulfate), filtered and concentrated to afford 0.428 g of 2-amino-5-bromo-N,N-dimethyl-benzamide as a pink solid, which was used without further purification.

Workup

  1. customThe vial was sealed
  2. concentrationafter which it was concentrated under vacuum
  3. dissolutionThe crude product was dissolved in Ethyl acetate
  4. washwashed 2× with water
  5. dry with materialThe organic phase was dried (Sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2dc2c558dcc6462485ae0a542adc7d56
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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