Pyridine → 1,3,5-Triiodobenzene-2,4,6-trialdehyde

HRID 1604140Notes

Reaction equation

HRID 1604140 reaction equation
[I:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([I:10])[C:5]([CH2:11][OH:12])=[C:4]([I:13])[C:3]=1[CH2:14][OH:15].C(N(CC)CC)C.N1C=CC=CC=1>CS(C)=O>[I:1][C:2]1[C:3]([CH:14]=[O:15])=[C:4]([I:13])[C:5]([CH:11]=[O:12])=[C:6]([I:10])[C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 206936271,3,5-Triiodo-2,4,6-trihydroxymethylbenzene

Product 1

HCID 184293191,3,5-Triiodobenzene-2,4,6-trialdehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

1,3,5-Triiodo-2,4,6-trihydroxymethylbenzene (4.5 g, 8.2 mmol) was dissolved in DMSO (80 ml). Triethylamine (51.7 ml, 371 mmol) and pyridine.SO3 (11.8 g, 74.2 mmol) were added and the mixture was stirred for two hours. The two phases were separated and the lower phase was cooled to 0° C., poured into water (150 ml) and stirred for 30 min at 0° C. The white solid was collected by filtration, washed with water and dried. Yield: 3.0 g (67%).

Workup

  1. additionSO3 (11.8 g, 74.2 mmol) were added
  2. customThe two phases were separated
  3. additionpoured into water (150 ml)
  4. stirringstirred for 30 min at 0° C
  5. filtrationThe white solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-eb14536febce4c24affa33efcc4711bc
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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