Acetic Acid → 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-diacetoxypropyl)amide chloride

HRID 1967636Notes

Reaction equation

HRID 1967636 reaction equation
[Cl-:1].[OH:2][CH:3]([CH2:26][OH:27])[CH2:4][NH:5][C:6](=[O:25])[C:7]1[C:15]([I:16])=[C:14]([NH:17][C:18](=[O:22])[CH2:19][O:20][CH3:21])[C:13]([I:23])=[C:9]([C:10]([OH:12])=[O:11])[C:8]=1[I:24].S(=O)(=O)(O)O.O.O.O.[C:36]([O-:39])(=O)[CH3:37].[Na+].O.[C:42](O)(=[O:44])[CH3:43]>>[Cl-:1].[C:42]([O:2][CH:3]([CH2:26][O:27][C:36](=[O:39])[CH3:37])[CH2:4][NH:5][C:6](=[O:25])[C:7]1[C:15]([I:16])=[C:14]([NH:17][C:18](=[O:22])[CH2:19][O:20][CH3:21])[C:13]([I:23])=[C:9]([C:10]([OH:12])=[O:11])[C:8]=1[I:24])(=[O:44])[CH3:43]

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 962WaterHCID 1118Sulfuric AcidHCID 23665404Sodium Acetate TrihydrateHCID 866509085-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride

Product 1

HCID 866509095-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-diacetoxypropyl)amide chloride

Conditions

Temperature
5 °C

Procedure

5-methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride (9.97 kg, 13.8 mol) was dispersed in acetic acid, and then anhydrous acetic acid (7.45 kg) was added thereto and the mixture was cooled to 5° C. Sulfuric acid (135 g) was slowly added thereto and the mixture was stirred for 1 hour. To the obtained clear solution, sodium acetate trihydrate (376 g) was added and dissolved at 0 to 5° C. And then water (96.6 kg) was added for 3 hours with maintaining 0 to 10° C. to produce solid. The produced solid was filtered and the title compound was obtained as a white solid (10.04 kg, yield 90.2%).

Workup

  1. dissolutiondissolved at 0 to 5° C
  2. temperaturewith maintaining 0 to 10° C.
  3. customto produce solid
  4. filtrationThe produced solid was filtered

Sources & evidence

ORD record
ord-61dd3212ebda43bd92bcc6bb755e0789
Source dataset
uspto-grants-2013_04
Patent number
US08420858B2

Reaction notes

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