Phenethyl isocyanate → HCID 67904965, compound

HRID 465638Notes

Reaction equation

HRID 465638 reaction equation
[CH2:1]([NH:19][CH2:20][C:21]([NH:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=1[O:34][CH3:35])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][N:44]=[C:45]=[O:46])=[CH:38][CH:37]=1>C(OCC)(=O)C>[CH2:1]([N:19]([C:45]([NH:44][CH2:43][CH2:42][C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)=[O:46])[CH2:20][C:21]([NH:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=1[O:34][CH3:35])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 160602Phenethyl isocyanateHCID 67904675HCID 67904675, compound

Product 1

HCID 67904965HCID 67904965, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.50 g of the product of Example 7, 0.2 g 2-phenethyl isocyanate, and a few mL ethyl acetate were briefly heated on the steambath and then allowed to sit 3 days at room temperature. The reaction mixture was then washed with dilute H3PO4, NaHCO3, and HaCl solutions, dried over MgSO4, filtered, and concentrated to an oil. The oil was chromatographed on SiO2 (70-230 mesh) using EtoAc as eluant. The product was obtained as an oil which crystallized on standing. 0.28 g (44%). NMR (CDCl3) δ 0.88 (3H, t), δ 1.25 (24H, m), δ 1.96 (4H, m) δ 2.84 (2H, t), δ 3.23 (2H, t), δ 3.51 (2H, q), δ 3.69 (6H, s), δ 3.77 (3H, s), δ 4.03 (2H, s), δ 4.70 (1H, t), δ 5.35 (2H, t), δ 6.13 (2H, s), δ 7.16-7.31 (5H, m), δ 7.46 (1H, s). IR (KBr) 3251, 2925, 1662, 1621, 1533, 1465, 1156, 1128, 810 cm-1.

Workup

  1. washThe reaction mixture was then washed with dilute H3PO4, NaHCO3, and HaCl solutions
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThe oil was chromatographed on SiO2 (70-230 mesh)
  6. customThe product was obtained as an oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-429fe8f295234d2d948b2d89cdcffdcd
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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