Acetic Anhydride → HCID 20309700, compound

HRID 437372Notes

Reaction equation

HRID 437372 reaction equation
[C:1]([C:4]1[C:5]([I:21])=[C:6]([C:15]([I:20])=[C:16]([NH2:19])[C:17]=1[I:18])[NH:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])([OH:3])=[O:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>Cl(O)(=O)(=O)=O>[C:1]([C:4]1[C:5]([I:21])=[C:6]([C:15]([I:20])=[C:16]([NH:19][C:22](=[O:24])[CH3:23])[C:17]=1[I:18])[NH:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20309687HCID 20309687, compound

Product 1

HCID 20309700HCID 20309700, compound

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

Potassium iododichloride (335 ml. 2.23N in water), was added over a period of forty minutes to a stirred suspension of 57.3 g. of 3'-carboxy-5'-aminosuccinanilic acid in 435 ml. of water. The solid product was collected by filtration and recrystallized from water and from aqueous dimethylformamide. The product was purified by converting it to the diammonium salt and then to the disodium salt, m.p. 222°-225° C. (dec.). The latter was acidified to produce the free acid form of 3'-carboxy-5'-amino-2',4',6'-triiodosuccinanilic acid, cream colored solid, m.p. 156.2°-172.2° C. (dec.). 3'-Carboxy-5'-amino-2',4',6'-triiodosuccinanilic acid can be acylated with acetic anhydride, using a few drops of perchloric acid as a catalyst to obtain 3'-carboxy-5'-acetamido-2',4',6'-triiodosuccinanilic acid [B; R is CH3CONH, R' and R" are H, Y' is CH2CH2, Z is OH].

Sources & evidence

ORD record
ord-94598ed32a8f47d68e8113c5b21aec2c
Source dataset
uspto-grants-1977_06
Patent number
US04031088

Reaction notes

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