Azane;hydrate → HCID 23446880, compound

HRID 992849Notes

Reaction equation

HRID 992849 reaction equation
[CH3:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:4]2[C:5](OC(=O)[NH:9][C:3]=12)=[O:6].O.[NH3:16]>CN(C=O)C.O>[NH2:9][C:3]1[C:2]([CH3:1])=[C:13]([Cl:14])[CH:12]=[CH:11][C:4]=1[C:5]([NH2:16])=[O:6]

Participants

5

Reactant 2

HCID 12896473Azane;hydrateHCID 57283159HCID 57283159, compound

Product 1

HCID 23446880HCID 23446880, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Using two inlets, at 80° C. a suspension of 4.64 g (0.0219 mol) of 3-methyl-4-chloroisatoic anhydride in 21 ml of DMF and 3.1 g (0.0219 mol) of 25% strength ammonia water in 6 ml of water were added simultaneously with stirring and over a period of 15 min to 8 ml of water. The mixture was stirred at 80° C. for 1 h and then cooled and extracted twice with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure, giving 2.61 g (64.4% of theory) of the title compound as colorless crystals of m.p. 206-208° C.

Workup

  1. additionwere added simultaneously
  2. temperaturecooled
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a97222c91bc142a79d32aea6d399e593
Source dataset
uspto-grants-2002_10
Patent number
US06472349B1

Reaction notes

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