Methylamine → HCID 67264205, compound

HRID 1688069Notes

Reaction equation

HRID 1688069 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=O)[O:9]C(=O)[NH:7][C:6]=2[C:13]=1[Cl:14].[CH3:15][NH2:16]>CN(C=O)C.CO>[NH2:7][C:6]1[C:13]([Cl:14])=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:10]([NH:16][CH3:15])=[O:9]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 33730957HCID 33730957, compound

Product 1

HCID 67264205HCID 67264205, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Crude 7,8-dichloro-1H-benzo[d][1,3]oxazine-2,4-dione (12.8 g) was dissolved in 50 mL of DMF and treated with 35 mL of 2 M methylamine in MeOH. The mixture was stirred at room temperature for 16 hours and extracted with methylene chloride. The organic phase was washed with brine, dried over by sodium sulfate, and concentrated. Chromatography on a silica gel column with methylene chloride and methanol (50:1) gave 1.0 g of 2-amino-3,4-dichloro-N-methyl-benzamide: 1H NMR (300 MHz, CDCl3) δ 7.12 (d, 1H), 6.71 (d, 1H), 6.27 (br, 2H), 6.04 (br, 1H), 2.96 (d, 3H); MS (m/e): 219.2 (M+1).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with brine
  3. dry with materialdried over by sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6ead50cc5d824057933cbff7e5832c29
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…