Acetoxyacetyl chloride → HCID 59824354, compound

HRID 1645490

Reaction equation

HRID 1645490 reaction equation
[CH2:1]([N:4]([CH3:20])[C:5]([C:7]1[C:8]([I:19])=[C:9]([C:13]([I:18])=[C:14]([NH2:17])[C:15]=1[I:16])[C:10]([Cl:12])=[O:11])=[O:6])[CH:2]=[CH2:3].[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>CC(N(C)C)=O>[CH2:1]([N:4]([CH3:20])[C:5]([C:7]1[C:15]([I:16])=[C:14]([NH:17][C:26]([CH2:25][O:24][C:21](=[O:23])[CH3:22])=[O:27])[C:13]([I:18])=[C:9]([C:10]([Cl:12])=[O:11])[C:8]=1[I:19])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 598243643-(Allyl-methyl-carbamoyl)-5-amino-2,4,6-triiodo-benzoyl chloride

Product 1

HCID 59824354HCID 59824354, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-(Allyl-methyl-carbamoyl)-5-amino-2,4,6-triiodo-benzoyl chloride (8) (5 g, 7.93 mmol) was dissolved in dry DMA (20 mL) was acetoxyacetyl chloride (1.7 mL, 15.9 mmol) was added dropwise. The reaction mixture was stirred at overnight at RT, with nitrogen bubbling through the reaction mixture. The reaction was monitored by TLC on silica gel plates eluting with ethyl acetate: petrol (1:1). (6) had an Rf of 0.62 and 0.76 whilst there were two new spots at 0.32 and 0.22. The solution was diluted with ethyl acetate (˜100 mL) and washed with ice water/brine (50:50, 20 ml×5). The organics were dried over MgSO4, filtered, concentrated and dried under high vacuum to give the desired compound (5.26 g, 91%). The structure was confirmed by 1H and 13C NMR, and purity by LCMS.

Workup

  1. additionwas added dropwise
  2. washeluting with ethyl acetate: petrol (1:1)
  3. additionThe solution was diluted with ethyl acetate (˜100 mL)
  4. washwashed with ice water/brine (50:50, 20 ml×5)
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-8d6405662a994c9d8c17afa5f36a0346
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Linked notes

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