Methoxyacetic Acid → 5-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride

HRID 1902604Notes

Reaction equation

HRID 1902604 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:11][C:12]1[C:13]([I:26])=[C:14]([C:23]([Cl:25])=[O:24])[C:15]([I:22])=[C:16]([C:20]=1[I:21])[C:17]([Cl:19])=[O:18]>CN(C=O)C>[CH3:1][O:2][CH2:3][C:4]([NH:11][C:12]1[C:20]([I:21])=[C:16]([C:17]([Cl:19])=[O:18])[C:15]([I:22])=[C:14]([C:13]=1[I:26])[C:23]([Cl:25])=[O:24])=[O:6]

Participants

5

Reactant 3

HCID 12251Methoxyacetic AcidHCID 24386Thionyl ChlorideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichloride

Product 1

HCID 135899615-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

121.2 g. (1.6 mole) of methoxyacetic acid is dissolved in 400 ml. of dry DMF, cooled to 0° C., and within 60 minutes 116 ml. (1.6 mol) of thionyl chloride is added dropwise thereto. The mixture is stirred for 30 minutes at 10° C. and 138.3 g. (0.4 mol) of 5-amino-2,4,6-triiodoisophthalic acid dichloride is introduced into the reaction mixture and the latter is stirred for 20 hours at room temperature. The reaction solution is stirred into 10 l. of water, the precipitate is vacuum-filtered, washed with water, again stirred with water, vacuum-filtered, and dried at 50° C. under vacuum. Yield: 198 g. (0.296 mol)=74% of theory.

Workup

  1. stirringthe latter is stirred for 20 hours at room temperature
  2. stirringThe reaction solution is stirred into 10 l
  3. filtrationof water, the precipitate is vacuum-filtered
  4. washwashed with water
  5. stirringagain stirred with water
  6. filtrationvacuum-filtered
  7. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-eb6b0fcccc954ca2bef50e86cfe2eb2c
Source dataset
uspto-grants-1982_12
Patent number
US04364921

Reaction notes

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