Water → HCID 22412553, compound

HRID 439659Notes

Reaction equation

HRID 439659 reaction equation
I[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([CH2:20]I)[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C-:29]#[N:30].[Na+].O.C[N:34]([CH:36]=O)C>>[CH2:14]([O:13][C:9]1[CH:10]=[CH:11][C:12]2[C:3]([CH2:2][C:29]#[N:30])=[C:4]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:5]=[CH:6][C:7]=2[C:8]=1[CH2:20][C:36]#[N:34])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 22412550HCID 22412550, compound

Product 1

HCID 22412553HCID 22412553, compoundYield 63%

Conditions

Temperature
-4 °C

Procedure

A mixture of 1,5-bis(iodomethyl)-2,6-dihexyloxynaphthalene (0.50 g, 0.83 mmol) and sodium cyanide (0.16 1.74 mmol) was stirred in DMF (50 ml) at 55° C. for 1 g, h. Water (50 ml) was added to the cooled mixture and the resulting precipitate was filtered, washed with water and dried. It was redissolved in a minimum of dichloromethane, hexane (40 ml) was added, and the solution was cooled to -4° C. overnight. The product was filtered to yield (14) (0.21 g, 63%), m.p. 135°-6° C.; 1H NMR (250.1 MHz, CDCl3) δ0.9-1.9 (22H, m, alkyl), 4.11 (4H, s, CH2CN), 4.14 (3H, t, J=7 Hz, CH2O), 7.35 and 7.88 (2H, 2d, J- 10 Hz, aromatic); 13C NMR. (62.9 Mhz, CDCl3) δ13.5, 14.2, 22.8, 25.9, 29.6, 31.7, 69.8, 112.2, 115.8, 118.3, 121.5, 127.9, 152.9; IR (KBr) vmax /cm-1 2248 w, 1598 s, 1261 s, 1067 s, 802 m. m/z 406 (M, 28), 238 (100), 91 (95).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customdried
  4. dissolutionIt was redissolved in a minimum of dichloromethane, hexane (40 ml)
  5. additionwas added
  6. filtrationThe product was filtered

Sources & evidence

ORD record
ord-908d7bd9be1e4e4aaff031f19b45ac7f
Source dataset
uspto-grants-1996_05
Patent number
US05514878

Reaction notes

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