Methylamine → HCID 67264205, compound

HRID 1041727Notes

Reaction equation

HRID 1041727 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-5102550a96464148875969ceeeaab5b1
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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