Methylamine → 3-Desbromo-3-chloro-Chlorantraniliprole

HRID 642588Notes

Reaction equation

HRID 642588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:26])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[C:13]([Cl:23])[CH:12]=3)[O:8][C:7](=[O:24])[C:6]=2[CH:25]=1.[CH3:27][NH2:28]>O1CCCC1>[Cl:23][C:13]1[CH:12]=[C:11]([C:9]([NH:10][C:5]2[C:6]([C:7]([NH:28][CH3:27])=[O:24])=[CH:25][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:26])=[O:8])[N:15]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:14]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 211133906-chloro-2-[3-chloro-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one

Product 1

HCID 116478403-Desbromo-3-chloro-Chlorantraniliprole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the benzoxazinone product of Example 8, Step E (6.32 g, 15.47 mmol) in tetrahydrofuran (50 mL) was added methylamine (2.0 M solution in THF, 38 mL, 77.38 mmol), and the reaction mixture was heated to 60° C., stirred for 1 hour and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford the title compound, a compound of the present invention, as a white solid (4.57 g) melting at 225-226° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe tetrahydrofuran solvent was evaporated under reduced pressure
  3. customthe residual solid was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ad97703d67b64da1b322c0a5a3b75937
Source dataset
uspto-grants-2010_04
Patent number
US07696233B2

Reaction notes

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