Sodium Iodide → HCID 18008958, compound

HRID 987524Notes

Reaction equation

HRID 987524 reaction equation
[CH2:1]([N:8]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])[CH2:9][CH2:10]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:26].[Na+]>CC(C)=O>[CH2:1]([N:8]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])[CH2:9][CH2:10][I:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 53866075HCID 53866075, compound

Product 1

HCID 18008958HCID 18008958, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulphonic acid 2-[benzyl-(4-bromo-2-nitro-phenyl)-amino]-ethyl ester (25 g, Reference Example 8) and sodium iodide (16.23 g) in anhydrous acetone (100 ml) was heated at reflux for 4 hours when a further portion of sodium iodide (8.12 g) was added and refluxing was continued for a further 16 hours. The reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C. and the residue was treated with distilled water (200 ml). The resulting mixture was extracted three times with dichloromethane (150 ml). The combined organic extracts were dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting brown oil (29,16 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting with a mixture of cyclohexane and ethyl acetate (9:1, v/v) to give the title compound (23.55 g) as a yellow oil. 1H NMR, 300 HMz, (CD3)2SO: δ3.3 (m, 4H); 4.4 (s, 2H); 7.25(m, 5H); 7.4 (d, J=8 Hz, 1H); 7.6 (dd, J=8 Hz and J=1.5 Hz, 1H); 8 (d, J=1.5 Hz, 1H). MS (EI): M+ 462 and 460 (5%), 445 and 443 (20%), 321 and 319 (10%), 91 (100%).

Workup

  1. temperaturewas heated
  2. additionwas added
  3. temperaturerefluxing
  4. customThe reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C.
  5. additionthe residue was treated with distilled water (200 ml)
  6. extractionThe resulting mixture was extracted three times with dichloromethane (150 ml)
  7. dry with materialThe combined organic extracts were dried over magnesium sulphate
  8. customevaporated under reduced pressure (2.7 kPa) at 40° C
  9. washeluting with a mixture of cyclohexane and ethyl acetate (9:1

Sources & evidence

ORD record
ord-8360763b117448a0ae3215d72db67fc1
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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