1,2-Dichloroethane → 2-Amino-3-bromo-5-methylbenzamide

HRID 908308Notes

Reaction equation

HRID 908308 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)CCl.C1C=[N:21]C2N(O)N=NC=2C=1.[Cl-].[NH4+].CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([NH2:21])=[O:5]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27744002-Amino-3-bromo-5-methylbenzoic acid

Product 1

HCID 588288742-Amino-3-bromo-5-methylbenzamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-amino-3-bromo-5-methylbenzoic acid (2.06 g, 8.95 mmol) was dissolved in DMF (19 ml) and EDC (2.10 g, 11.0 mmol), HOAt (1.56 g, 11.5 mmol), ammonium chloride (2.03 g, 38.0 mmol), and iPr2NEt (6.5 ml, 37.3 mmol) were added. The reaction was stirred at room temperature under nitrogen for 21.5 hours, and then poured into water (50 ml), resulting in the formation of a precipitate. The suspension was filtered and the solid was washed with water and dried in vacuo to give title compound (1.83 g, 89%). MS (ESI pos. ion) m/z: 229 (M+H). Calc'd Exact Mass for C8H9BrN2O: 228.

Workup

  1. customresulting in the formation of a precipitate
  2. filtrationThe suspension was filtered
  3. washthe solid was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9093f35b167a4834a7cfc00ac1b92d4d
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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