Sulfuric Acid → HCID 22749364, compound

HRID 1834170Notes

Reaction equation

HRID 1834170 reaction equation
[NH2:1][C:2]1[C:3]([I:23])=[C:4]([C:13]([NH:15][C:16]([CH2:21][OH:22])([CH2:19][OH:20])[CH2:17][OH:18])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.C(O[C:33](=[O:35])[CH3:34])(=O)C>>[C:7]([NH:1][C:2]1[C:3]([I:23])=[C:4]([C:13]([NH:15][C:16]([CH2:17][O:18][C:33](=[O:35])[CH3:34])([CH2:19][O:20][C:17](=[O:18])[CH3:16])[CH2:21][O:22][C:13](=[O:14])[CH3:4])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([OH:9])=[O:8])(=[O:8])[CH3:6]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 22749361HCID 22749361, compound

Product 1

HCID 22749364HCID 22749364, compound

Procedure

5-Amino-2,4,6-triiodo-N-[tris(hydroxymethyl)methyl]isophthalamic acid (50.0 g., 0.076 mol.) was added in one portion to a stirred solution of sulfuric acid (0.36 ml.) in acetic anhydride (136.0 ml.). The temperature of the reaction mixture rose briefly to 82° and dissolution was effected. As the reaction mixture cooled to room temperature, the product began to precipitate at 47° and the mixture was diluted with toluene (100 ml.). The mixture was stirred at room temperature for 1 hr., and filtered. The filter cake was washed with toluene (50 ml.), dried, dissolved in hot methanol (300 ml.), and treated with charcoal (6 g.). After removal of the charcoal, the product precipitated from the cold station and was collected and dried (70° ) to give white crystalline 5-acetamido-2,4,6-triiodo-N-[tris(acetoxymethyl)methyl]-isophthalamic acid (38.8 g.) m.p. 248-251 (dec., uncorr.). (Yield, 62%). This material was pure by TLC analysis (benzene, 2-butanone, 88% formic acid; 60:25:20) and its structure was confirmed by IR and NMR. Anal. Calcd. for C20H21I3N2O10 : C, 28.94; H, 2.55; N.E., 830.12. Found: C, 29.02; H, 2.70; N.E., 825.6.

Workup

  1. customrose briefly to 82°
  2. dissolutiondissolution
  3. customto precipitate at 47°
  4. additionthe mixture was diluted with toluene (100 ml.)
  5. filtration, and filtered
  6. washThe filter cake was washed with toluene (50 ml.)
  7. customdried
  8. dissolutiondissolved in hot methanol (300 ml.)
  9. additiontreated with charcoal (6 g.)
  10. customAfter removal of the charcoal
  11. customthe product precipitated from the cold station
  12. customwas collected
  13. customdried (70° )

Sources & evidence

ORD record
ord-4f8512021f59460e9af707c6834b86c0
Source dataset
uspto-grants-1978_01
Patent number
US04069250

Reaction notes

Loading…