Sodium Iodide → HCID 67971984, compound

HRID 41884Notes

Reaction equation

HRID 41884 reaction equation
[I-:1].[Na+].Cl[C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[CH2:10][N:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][C:5]=12>C(#N)C>[I:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[CH2:10][N:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][C:5]=12

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66995010953045-41-5

Product 1

HCID 67971984HCID 67971984, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium iodide (3.93 g, 26.2 mmol) and Ex 11-Step 1 product, hydrochloride salt (step 1, 2.30 g, 8.74 mmol) in acetonitrile (20 mL) were refluxed for 3 days. The reaction mixture was cooled, concentrated and partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The phases were separated and the aqueous phase was re-extracted twice with CH2Cl2 (total volume 750 mL). The solution was passed through a plug of silica gel (0.5″) layered with celite (0.5″) using 1:1 EtOAc/CH2Cl2 for elution to yield 1.98 g (71%) of Ex 11-Step 2 product as a brown solid: 1H NMR shows a ˜1:1 mixture of rotamers (400 MHz, CDCl3) δ 8.08-8.11 (overlapping doublets, 1H total), 7.61 (br d, J=5.3, 1H), 4.89/4.84 (br singlets, 2H total), 4.68/4.64 (br singlets, 2H total), 4.23-4.29 (overlapping quartets, 2H total), 1.32-1.37 (overlapping triplets, 3H total).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompartitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  4. customThe phases were separated
  5. extractionthe aqueous phase was re-extracted twice with CH2Cl2 (total volume 750 mL)
  6. washfor elution
  7. customto yield 1.98 g (71%) of Ex 11-Step 2 product as a brown solid
  8. additiona ˜1:1 mixture of rotamers (400 MHz, CDCl3) δ 8.08-8.11 (overlapping doublets, 1H total), 7.61 (br d, J=5.3, 1H), 4.89/4.84 (br singlets, 2H total), 4.68/4.64 (br singlets, 2H total), 4.23-4.29 (overlapping quartets, 2H total), 1.32-1.37 (overlapping triplets, 3H total)

Sources & evidence

ORD record
ord-6abf26902cf14dd4a38565f8a6438e29
Source dataset
uspto-grants-2013_09
Patent number
US08536164B2

Reaction notes

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