Methanol → HCID 66854326, compound

HRID 251925Notes

Reaction equation

HRID 251925 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([CH3:14])[C:5]2[NH:6]C(=O)O[C:9](=[O:10])[C:4]=2[CH:3]=1.[C:15]([O:19][CH3:20])(=[O:18])[NH:16][NH2:17].CO>O>[NH2:6][C:5]1[C:12]([CH3:14])=[CH:13][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]([NH:17][NH:16][C:15]([O:19][CH3:20])=[O:18])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 80519Methyl carbazateHCID 115502595-Chloro-3-methyl isatoic anhydride

Product 1

HCID 66854326HCID 66854326, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.05 g of 6-chloro-8-methyl-1H-benzo[d]-1,3-oxazine-2,4-dione, 0.46 g of methyl carbazate and 20 ml of methanol was heated to reflux for 3 hours. After the reaction mixture was allowed to cool to around room temperature, water was poured thereto and the mixture was extracted with ethyl acetate three times. The resulting organic layer was concentrated under reduced pressure, and the residue was washed with toluene to obtain 0.77 g of N-(2-amino-5-chloro-3-methylbenzoyl)-N′-methoxycarbonylhydrazine of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool to around room temperature
  4. extractionthe mixture was extracted with ethyl acetate three times
  5. concentrationThe resulting organic layer was concentrated under reduced pressure
  6. washthe residue was washed with toluene

Sources & evidence

ORD record
ord-edb1e9fb023140cda37768f2d9730a17
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…