Methoxyacetic Acid → N-methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid dichloride

HRID 1902606Notes

Reaction equation

HRID 1902606 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.O=S(Cl)Cl.[CH3:11][NH:12][C:13]1[C:14]([I:27])=[C:15]([C:24]([Cl:26])=[O:25])[C:16]([I:23])=[C:17]([C:21]=1[I:22])[C:18]([Cl:20])=[O:19]>CC(N(C)C)=O>[CH3:1][O:2][CH2:3][C:4]([N:12]([C:13]1[C:21]([I:22])=[C:17]([C:18]([Cl:20])=[O:19])[C:16]([I:23])=[C:15]([C:14]=1[I:27])[C:24]([Cl:26])=[O:25])[CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 12251Methoxyacetic AcidHCID 24386Thionyl ChlorideHCID 214667042,4,6-Triiodo-5-(methylamino)-1,3-benzenedicarbonyl dichloride

Product 1

HCID 17887369N-methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid dichloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

30 ml. (400 mmol) of methoxyacetic acid is dissolved in 100 ml. of DMA, cooled to 0° C., and 29 ml. (400 mmol) of SOCl2 is added dropwise. The mixture is stirred for 30 minutes at this temperature, a solution of 61 g. (100 mmol) of 5-methylamino-2,4,6-triiodoisophthalic acid dichloride in 200 ml. of DMA is added dropwise thereto, and the reaction solution is stirred for 20 hours at room temperature. Then, the solution is stirred into 4 l. of water, the precipitate is vacuum-filtered, dissolved in 2 l. of ethyl acetate, successively extracted with respectively 250 ml. of saturated bicarbonate solution, saturated sodium chloride solution, and water; the ethyl acetate phase is dried over Na2SO4 and evaporated. Yield: 61.4 g. (90 mmol)=90% of theory.

Workup

  1. stirringthe reaction solution is stirred for 20 hours at room temperature
  2. stirringThen, the solution is stirred into 4 l
  3. filtrationof water, the precipitate is vacuum-filtered
  4. dissolutiondissolved in 2 l
  5. extractionof ethyl acetate, successively extracted with respectively 250 ml
  6. dry with materialthe ethyl acetate phase is dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-3714dd475761416590b77c2cc8ffa5b3
Source dataset
uspto-grants-1982_12
Patent number
US04364921

Reaction notes

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