Phenyl isocyanate → 5-Benzyl-3-dodecylisoxazole

HRID 2380522Notes

Reaction equation

HRID 2380522 reaction equation
[C:1]1([CH2:7][C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=O)C=CC=CC=1.[N+:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([O-])=[O:20].C(N(CC)CC)C>C1C=CC=CC=1>[CH2:23]([C:22]1[CH:9]=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:20][N:19]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 575753BenzylacetyleneHCID 108233151-Nitrotridecane

Product 1

HCID 105923395-Benzyl-3-dodecylisoxazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a room temperature, stirred solution of 3-phenyl-1-propyne (54.86 g, 0.4723 mol) and phenyl isocyanate (104 mL, 0.957 mol) in benzene (800 mL) under nitrogen was added dropwise over 30 minutes a solution of 1-nitrotridecane (109.14 g, 0.47583 mol) and triethylamine (6.7 mL, 0.048 mol) in benzene (400 mL), and the mixture was stirred for 1 hour. The mixture was refluxed for 6 hours, allowed to cool, and chilled. The solids were filtered off and the filtrate rotoevaporated to an oil. The oil was chromatographed on silica gel (1.4 kg, 230-400 mesh) using petroleum ether-ether (25:1, 15×1 L), and product fractions rotoevaporated to give an off-white solid; yield 96.1 g (62%), mp 45°-47° C.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperatureto cool
  3. temperaturechilled
  4. filtrationThe solids were filtered off
  5. customThe oil was chromatographed on silica gel (1.4 kg, 230-400 mesh)
  6. customto give an off-white solid

Sources & evidence

ORD record
ord-391bad73f9274b5396aff3653112427c
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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