Azane;hydrate → HCID 23446880, compound

HRID 1841632Notes

Reaction equation

HRID 1841632 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

Procedure

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 allowed to run simultaneously at 80° C., over 2 additions, into 8 ml of water with stirring in the course of 15 min. After stirring at 80° C. for 1 h, the mixture was cooled and extracted 2× with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated in vacuo, 2.61 g (64.4% of theory) of the title compound being obtained as colorless crystals of m.p. 206-208° C.

Workup

  1. stirringAfter stirring at 80° C. for 1 h
  2. temperaturethe mixture was cooled
  3. extractionextracted 2× with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo, 2.61 g (64.4% of theory) of the title compound
  6. custombeing obtained as colorless crystals of m.p. 206-208° C.

Sources & evidence

ORD record
ord-de7032f96a214a198c543f08a0c78998
Source dataset
uspto-grants-2004_01
Patent number
US06683213B1

Reaction notes

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