Dimethylformamide → 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride
Reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:8]([I:21])=[C:9]([C:18](Cl)=[O:19])[C:10]([I:17])=[C:11]([C:15]=1[I:16])[C:12]([Cl:14])=[O:13])=[O:5].C(N(CCCC)CCCC)CCC.[OH:35][CH:36]([CH2:39][OH:40])[CH2:37][NH2:38].CN(C=[O:45])C>>[Cl-:14].[OH:35][CH:36]([CH2:39][OH:40])[CH2:37][NH:38][C:18](=[O:19])[C:9]1[C:8]([I:21])=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:15]([I:16])=[C:11]([C:12]([OH:45])=[O:13])[C:10]=1[I:17]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
50 g. (75 mmol) of 5-methoxyacetylamino-2,4,6-triiodoisophthalic acid dichloride is dissolved in 200 ml. of dry DMF; 18 g. (97.3 mmol) of tributylamine is added thereto, the mixture is heated to 60° C., and, at this temperature, a solution of 7.5 g. (82.4 mmol) of 2,3-dihydroxypropylamine in 50 ml. of DMF is added dropwise thereto. The mixture is stirred for 2 hours at 60° C., then concentrated to 100 ml., and stirred into 1.2 l. of methylene chloride. The precipitate thus formed is vacuum-filtered, dried, refluxed twice with respectively 500 ml. of ethyl acetate, and filtered in the hot state. The evaporated filtrate yields 40.5 g. (56 mmol)=74.5% of theory of the desired product as a colorless solid.
Workup
- concentrationconcentrated to 100 ml
- stirring, and stirred into 1.2 l
- customThe precipitate thus formed
- filtrationis vacuum-filtered
- customdried
- temperaturerefluxed twice with respectively 500 ml
- filtrationof ethyl acetate, and filtered in the hot state
- customThe evaporated filtrate yields 40.5 g
Sources & evidence
- ORD record
- ord-875430f714694d3185cad83fec7dfa28
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04364921
Reaction notes
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