2,6-Diisopropylphenyl isocyanate → HCID 67904786, compound

HRID 465639Notes

Reaction equation

HRID 465639 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]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH:45]([CH3:47])[CH3:46])[C:40]=1[N:48]=[C:49]=[O:50])([CH3:38])[CH3:37].[K+].[Br-]>C(OCC)(=O)C>[CH3:38][CH:36]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH:45]([CH3:46])[CH3:47])[C:40]=1[NH:48][C:49]([N: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])[CH2:1][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])=[O:50])[CH3:37]

Participants

5

Reactant 3

HCID 922592,6-Diisopropylphenyl isocyanateHCID 253877Potassium BromideHCID 67904675HCID 67904675, compound

Product 1

HCID 67904786HCID 67904786, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.50 g of the product of Example 7, 0.22 g 2,6-diisopropylphenylisocyanate and a few mL ethyl acetate was allowed to sit 3 days at room temperature. The solvent was removed and the residue chromatographed on SiO2 (70-230 mesh) using hexane/EtoAc, 1/1, as eluant. The product was obtained as a white solid. 0.33 g (46%). NMR (CDCl3) δ 0.88 (3H, t), δ 1.15 (12H, d), δ 1.21-1.26 (22H, m) δ 1.78 (2H, m), δ 2.02 (4H, m), δ 3.10 (2H, m), δ 3.47 (2H, t), δ 3.75 (6H, s), δ 3.80 (3H, s), δ 4.17 (2H, s), δ 5.35 (2H, t), δ 6.07 (1H, s), δ 6.14 (2H, s), δ 7.13-7.25 (3H, m), δ 7.72 (1H, s). IR (KBr) 3242, 2959, 2525, 1675, 1627, 1508, 1156, 1135 cm-1.

Workup

  1. customThe solvent was removed
  2. customthe residue chromatographed on SiO2 (70-230 mesh)
  3. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-c32a605b65d349a69812b350566710a8
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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