2,5-dibromopentanoyl Bromide → N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl)ethyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233073Notes

Reaction equation

HRID 233073 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][Br:9])[C:3](Br)=[O:4].[C:10]([O:13][CH2:14][CH:15]([NH:21][C:22]([C:24]1[C:29]([I:30])=[C:28]([NH2:31])[C:27]([I:32])=[C:26]([C:33]([NH:35][CH:36]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:37][O:38][C:39](=[O:41])[CH3:40])=[O:34])[C:25]=1[I:47])=[O:23])[CH2:16][O:17][C:18](=[O:20])[CH3:19])(=[O:12])[CH3:11]>CC(N(C)C)=O>[C:44]([O:43][CH2:42][CH:36]([NH:35][C:33]([C:26]1[C:27]([I:32])=[C:28]([NH:31][C:3](=[O:4])[CH:2]([Br:1])[CH2:6][CH2:7][CH2:8][Br:9])[C:29]([I:30])=[C:24]([C:22]([NH:21][CH:15]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:14][O:13][C:10](=[O:12])[CH3:11])=[O:23])[C:25]=1[I:47])=[O:34])[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:46])[CH3:45]

Participants

4

Reactant 2

HCID 111630822,5-dibromopentanoyl BromideHCID 11766168N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 19048392N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl)ethyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,5-Dibromopentanoyl bromide prepared as described in example 8a (15.9 g, 49.3 mmol) was added dropwise to a stirred solution of N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (33 g, 37.8 mmol) in dimethylacetamide (250 ml) at 0°. After the addition, the reaction mixture was stirred at 0° for 1 hour, and then at room temperature for 22 hours. The solution was then added slowly dropwise to a well stirred mixture of ice-water (2 L), when a white solid separated out. This was collected by filtration, washed with ice-water (3×50 ml), and dried in vacuo to obtain the crude product (40.1 g, 91.5% pure). Recrystallization from ethyl acetate furnished analytically pure N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide as an off-white crystalline compound (35.3 g, 84% yield), m.p. 240°-243°.

Workup

  1. additionAfter the addition
  2. waitat room temperature for 22 hours
  3. additionThe solution was then added slowly dropwise to a well
  4. stirringstirred
  5. customseparated out
  6. filtrationThis was collected by filtration
  7. washwashed with ice-water (3×50 ml)
  8. customdried in vacuo
  9. customto obtain the crude product (40.1 g, 91.5% pure)
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f454ae7b46b448f1b872a232eccdcc7e
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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