Ammonia → HCID 10059905, compound

HRID 1199367Notes

Reaction equation

HRID 1199367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1[Cl:13].[NH3:14]>C1COCC1>[C:9]([C:4]1[CH:3]=[C:2]([Cl:1])[C:12]([Cl:13])=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])(=[O:10])[NH2:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 703344,5-Dichlorophthalic anhydride

Product 1

HCID 10059905HCID 10059905, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dichlorophthalic acid, anhydride (20.0 g, 92.2 mmol) was dissolved in dry THF (400 mL) and cooled in an ice bath. Ammonia gas was then passed through this solution for 10 minutes to afford a precipitate. The THF was removed and water (400 mL) was added. This aqueous solution was brought to acidic pH with 10% aqueous HCl whereupon a precipitate appeared. This solid was collected, washed with water and dried in vacuo to provide the product (17.3 g, 80%) as a tan solid, m.p. 197°-201° C.

Workup

  1. temperaturecooled in an ice bath
  2. customto afford a precipitate
  3. customThe THF was removed
  4. additionwater (400 mL) was added
  5. customThis solid was collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1802b26768c5407581f6a926217c26d4
Source dataset
uspto-grants-1990_02
Patent number
US04900739

Reaction notes

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