Sodium Iodide → HCID 22492580, compound

HRID 2253539Notes

Reaction equation

HRID 2253539 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[Na+].[I-:24].CN[C@@H]1CCCC[C@H]1NC.O1CCOCC1>N.[Cu]I.O>[I:24][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 967402-(3-Bromophenyl)-5-(2-naphthyl)-1,3,4-oxadiazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 22492580HCID 22492580, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 2-(3-bromophenyl)-5-(2-naphthyl)-1,3,4-oxadiazole (352 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), briefly evacuated and backfilled with argon. Racemic trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. The resulting light green-gray suspension was allowed to reach room temperature, diluted with 30% aq ammonia (5 mL), poured into water (20 mL), and extracted with dichloromethane (3×15 mL). The combined organic phases were dried (Na2SO4), concentrated to ca. 2 mL volume. The product was allowed to crystallize at room temperature. After 15 min, hexane (20 mL) was added, the mixture was kept at room temperature for 15 h, and finally filtered to provide 382 mg (96% yield) of 2-(3-iodophenyl)-5-(2-naphthyl)-1,3,4-oxadiazole as white, fine needles. Mp: 156-158° C. 1H NMR (400 MHz, CDCl3): δ 8.64 (s, I H), 8.53 (t, J=1.8 Hz, 1H), 8.22 (dd, J=8.6, 1.8 Hz, 1H), 8.18 (dt, J=7.9, 1.2 Hz, 1H), 8.03-7.93 (m, 2H), 7.95-7.88 (m, 2H), 7.65-7.53 (m, 2H), 7.30 (t, J=7.9 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ 165.1, 163.2, 140.6, 135.5, 134.8, 132.8, 130.7, 129.1, 128.9, 128.1, 128.0, 127.5, 127.2, 126.1, 125.8, 123.2, 120.8, 94.4. IR (neat, cm−1): 1558, 1540, 753, 731. Anal. Calcd. for C18H11IN2O: C, 54.29; H, 2.78. Found: C, 54.29; H, 2.74.

Workup

  1. custombriefly evacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. extractionextracted with dichloromethane (3×15 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated to ca. 2 mL volume
  7. customto crystallize at room temperature
  8. waitAfter 15 min
  9. additionhexane (20 mL) was added
  10. waitthe mixture was kept at room temperature for 15 h
  11. filtrationfinally filtered

Sources & evidence

ORD record
ord-d84e96ed6ccd4d9a85e41c9d0221b1b4
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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