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

HRID 2388969Notes

Reaction equation

HRID 2388969 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].O1CCCC1>>[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 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 509995122-Amino-5-bromo-N,N-dimethylbenzamideYield 78.6%

Conditions

Temperature
60 °C

Procedure

A 350 ml round bottomed pressure tube was charged with 5-bromoisatoic anhydride (15.0 g, 62.0 mmol) and 2 M dimethylamine in tetrahydrofuran (90 ml, 180 mmol). The vial was sealed and heated in an oil bath at 60° C. for 1 hour, then concentrated to dryness. The residue was dissolved in dichloromethane (100 ml). The organic layer was washed with saturated, aqueous sodium bicarbonate solution (25 ml), and water (25 ml), then dried over sodium sulfate and concentrated to obtain a yellow powder. The powder was re-crystallized from ether to obtain 11.8 g (78.6%) of 2-amino-5-bromo-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, CDCl3) δ 7.20 (dd, J=8.5, 2.5 Hz, 1H), 7.10 (d, J=2.5 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 5.34 (s, 2H), 2.91 (s, 6H); MS: m/z 243.1, 245.1 (M+H+).

Workup

  1. customThe vial was sealed
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. washThe organic layer was washed with saturated, aqueous sodium bicarbonate solution (25 ml), and water (25 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto obtain a yellow powder
  8. customThe powder was re-crystallized from ether

Sources & evidence

ORD record
ord-6089d0f23a12451089ce220f714383a1
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

Loading…