Pyridine → HCID 19737610, compound

HRID 2255650Notes

Reaction equation

HRID 2255650 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[I:9][C:10]1[CH:11]=[C:12]2[C:17](=O)[O:16][C:14](=[O:15])[C:13]2=[CH:19][CH:20]=1.N1C=CC=CC=1.C(OC(=O)C)(=O)C>O.CC(N(C)C)=O>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:17](=[O:16])[C:12]3=[CH:11][C:10]([I:9])=[CH:20][CH:19]=[C:13]3[C:14]2=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 108934-IodoanilineHCID 152633775-Iodo-2-benzofuran-1,3-dione

Product 1

HCID 19737610HCID 19737610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

##STR19## A 100 milliliter round-bottomed flask, equipped with stirrer, was charged with p-iodoaniline (10.95 grams, 0.05 mol) and dimethylacetamide (DMAc) (35 milliliters). 4-iodophthalic anhydride (13.6 grams, 0.05 mol) was added slowly over 10 minutes. The reaction mixture was heated with stirring to a temperature of about 70° C. Pyridine (19.45 grams, 0.25 mol) was added, the reaction mixture was stirred for 15 minutes, then acetic anhydride (11.12 grams, 0.11 mol) was added dropwise over 20 minutes. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was poured into water, producing a white solid product, which was collected by filtration, triturated with methanol (300 milliliters) and dried under vacuum at 60° C. overnight. Melting point, as determined by DSC was 235° C. Combustion analysis was: calculated: C=35.40, H=1.49, N=2.95; measured: C=35.47, H=1.59, N=2.94. Proton NMR was consistent with the above general structure.

Workup

  1. custom##STR19## A 100 milliliter round-bottomed flask, equipped with stirrer
  2. temperatureThe reaction mixture was heated
  3. stirringthe reaction mixture was stirred for 15 minutes
  4. stirringThe reaction mixture was stirred at 70° C. overnight
  5. customproducing a white solid product, which
  6. filtrationwas collected by filtration
  7. customtriturated with methanol (300 milliliters)
  8. customdried under vacuum at 60° C. overnight
  9. customwas 235° C

Sources & evidence

ORD record
ord-9ff793e2ac0b4ffcb65128a1e6821e0d
Source dataset
uspto-grants-1993_08
Patent number
US05241038

Reaction notes

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