Thionyl Chloride → 4-Chloro-3-iodobenzamide

HRID 2357635Notes

Reaction equation

HRID 2357635 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[I:11].S(Cl)(Cl)=O.O1CCOCC1.C([N:25](C(C)C)CC)(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:25])=[O:7])=[CH:4][C:3]=1[I:11]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 27576164-Chloro-3-iodobenzoic acid

Product 1

HCID 221155764-Chloro-3-iodobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-chloro-3-iodobenzoic acid (2.09 g, 7.40 mmol) was suspended in thionyl chloride (0.540 mL, 7.40 mmol) and heated to 70° C. for 3 h before it was concentrated and azeotropically dried with toluene. The concentrate was dissolved in ammonia, 0.5 M in 1,4-dioxane (92.5 mL, 37.0 mmol) to which diisopropylethylamine (6.44 mL, 37.0 mmol) was added and it was stirred at RT for 3 h. The mixture was diluted with 100 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 4 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 282 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. dry with materialazeotropically dried with toluene
  3. dissolutionThe concentrate was dissolved in ammonia
  4. additionadded to a separation funnel
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washwashed 4 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26595a7b65764db5be0882124cf4959c
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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