Ammonia → HCID 10005127, compound

HRID 482135Notes

Reaction equation

HRID 482135 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:5]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:4][C:3]=1Br.[Cu][C:34]#[N:35].N.[CH3:37][N:38](C=O)C>>[CH2:20]([O:19][C:5]1[CH:4]=[C:3]([C:34]#[N:35])[C:2](=[CH:7][C:6]=1[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:37]#[N:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 10257667HCID 10257667, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 10005127HCID 10005127, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 1,2-dibromo-4-dodecyloxy-5-(1,4,7,10-tetraoxaundecyl)benzene (4.5 g, 7.7 mmole) and copper (I) cyanide (2.1 g, 23 mmoles) in anhydrous DMF (50 ml) was heated and stirred at 150° C. for 48 h under a nitrogen atmosphere. The mixture was carefully poured into rapidly stirred concentrated aqueous ammonia solution (300 ml). After 1 h, the precipitate was filtered and washed with ammonia solution (50 ml) and water (200 ml). The resultant solid was dried and then passed down a silica column (ethyl acetate/petrol, 2:5) to give 4-dodecyloxy-5-(1,4,7,10-tetraoxaundecyl)-phthalonitrile as white needles (1.7 g, 47%), m.p. 38°-40° C.(recrystallised from methanol/water), (Found C, 68.20; H, 9.00; N, 6.10, C27H42 N2O5 requires C,68.32; H, 8.92; N, 5.90); MS (CI) m/e 492 (M+ +NH4+); δH (200 MHz, CDCl3) 0.85(t, 3H), 1.23(br s, 18H), 1.83(q, 2H), 3.35 (s, 3H), 3.63 (m, 8H), 3.89 (t, 2H), 4.03 (t, 2H), 4.23(t, 2H), 7.12 (s, 1H), and 7.23 (s, 1H) and 4-dodecyloxy-5-(1,4,7,10-tetraoxaundecyl)phthalimide (0.27 g, 6%) as small white needles, m.p. 73°-74° C. (recrystallised from methanol/water), (Found C, 65.70; H, 8.78; N, 2.70, C27H43 NO7 requires C,65.69; H, 8.78; N, 2.70); MS (CI) m/e 511 (M+ +NH4+); δH (200 MHz, CDCl3) 0.85(t, 3H), 1.27(br s, 18H), 1.85(q, 2H), 3.38 (s, 3H), 3.66 (m, 8H), 3.93 (t, 2H), 4.09 (t, 2H), 4.27(t, 2H), 7.27 (s, 1H), 7.30 (s, 1H) and 7.34 (s, 1H).

Workup

  1. temperaturewas heated
  2. additionThe mixture was carefully poured
  3. waitAfter 1 h
  4. filtrationthe precipitate was filtered
  5. washwashed with ammonia solution (50 ml) and water (200 ml)
  6. customThe resultant solid was dried
  7. customto give
  8. custom4-dodecyloxy-5-(1,4,7,10-tetraoxaundecyl)-phthalonitrile as white needles (1.7 g, 47%), m.p. 38°-40° C.(recrystallised from methanol/water), (Found C, 68.20; H, 9.00; N, 6.10, C27H42 N2O5 requires C,68.32; H, 8.92; N, 5.90)
  9. customδH (200 MHz, CDCl3) 0.85(t, 3H), 1.23(br s, 18H), 1.83(q, 2H), 3.35 (s, 3H), 3.63 (m, 8H), 3.89 (t, 2H), 4.03 (t, 2H), 4.23(t, 2H), 7.12 (s, 1H), and 7.23 (s, 1H) and 4-dodecyloxy-5-(1,4,7,10-tetraoxaundecyl)phthalimide (0.27 g, 6%) as small white needles, m.p. 73°-74° C. (recrystallised from methanol/water), (Found C, 65.70; H, 8.78; N, 2.70, C27H43 NO7 requires C,65.69; H, 8.78; N, 2.70)

Sources & evidence

ORD record
ord-964e4ee661304848a0799af555b861be
Source dataset
uspto-grants-1998_08
Patent number
US05792860

Reaction notes

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