Sodium Iodide → HCID 86615735, compound

HRID 1788262Notes

Reaction equation

HRID 1788262 reaction equation
[C:1](=[O:13])([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:2][CH:3](Cl)[CH3:4].[C:14]([OH:19])(=[O:18])[CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C.[I-].[Na+]>C(OCC)C>[C:1](=[O:13])([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:2][CH:3]([O:19][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 3249365HCID 3249365, compound

Product 1

HCID 86615735HCID 86615735, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of compound (4) (10 g, 46 mmol), isobutyric acid (30 mL), triethylamine (30 mL) and sodium iodide (2 g) was stirred and heated in an oil bath at 50° C. for 3 days. The reaction mixture was diluted with diethyl ether (200 mL) and washed successively with water (3×100 mL), saturated aqueous sodium bicarbonate (2×100 mL) and 0.1 M aqueous potassium bisulfate (2×100 mL). The organic phase was separated, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound (9) as a pale yellow liquid (12 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 1.2 (d, 6H), 1.5 (d, 3H), 2.55 (m, 1H), 6.95 (q, 1H), 7.4-7.5 (m, 5H).

Workup

  1. washwashed successively with water (3×100 mL), saturated aqueous sodium bicarbonate (2×100 mL) and 0.1 M aqueous potassium bisulfate (2×100 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a51be63b2354a1997c8f41ee5285522
Source dataset
uspto-grants-2009_03
Patent number
US07511158B2

Reaction notes

Loading…