Propanoyl bromide, 2-bromo- → HCID 86606430, compound

HRID 131994Notes

Reaction equation

[NH2:1][CH2:2][C:3]([NH:5][CH2:6][CH2:7][N:8]([CH2:25][CH2:26][NH:27][C:28](=[O:31])[CH2:29][NH2:30])[C:9](=[O:24])[C:10]1[C:18]([I:19])=[C:17]([NH:20][CH3:21])[C:16]([I:22])=[C:12]([C:13]([OH:15])=[O:14])[C:11]=1[I:23])=[O:4].[Br:32][CH:33]([CH3:37])[C:34](Br)=[O:35]>CC(N(C)C)=O>[Br:32][CH:33]([CH3:37])[C:34]([NH:30][CH2:29][C:28]([NH:27][CH2:26][CH2:25][N:8]([CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH2:2][NH:1][C:34](=[O:35])[CH:33]([Br:32])[CH3:37])[C:9](=[O:24])[C:10]1[C:18]([I:19])=[C:17]([NH:20][CH2:21][C:34](=[O:35])[CH:33]([Br:32])[CH3:37])[C:16]([I:22])=[C:12]([C:13]([OH:15])=[O:14])[C:11]=1[I:23])=[O:31])=[O:35]

Participants

Conditions

Temperature: 40 °C

Procedure

57.8 g (75 mmol) of N,N-bis-[2-(2-aminoacetylamino)ethyl]-5-(methylamino)-2,4,6-triiodoisophthalic acid amide is dissolved in 500 ml of dimethylacetamide, and 75.5 g (350 mmol) of 2-bromopropionic acid bromide (Aldrich) is added in drops over 15 minutes at 0° C. Then, it is stirred for 20 hours at 40° C. The reaction mixture is poured into 4000 ml of ice water, the solid that accumulates is filtered off, dissolved in 800 ml of ethyl acetate and extracted three times with 250 ml each of water. The organic phase is dried on sodium sulfate, and the solvent is evaporated to the dry state. The crude product is recrystallized from methyl-tert-butyl ether.

Workup

filtrationthe solid that accumulates is filtered off
dissolutiondissolved in 800 ml of ethyl acetate
extractionextracted three times with 250 ml each of water
customThe organic phase is dried on sodium sulfate
customthe solvent is evaporated to the dry state
customThe crude product is recrystallized from methyl-tert-butyl ether

Sources & evidence

ORD record: ord-f719b7b5fd744a2481307145517e89c3
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07385054B2

Reaction notes

Loading…