2,6-Diisopropylphenyl isocyanate → HCID 19874880, compound

HRID 465635Notes

Reaction equation

HRID 465635 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]=[O:15])([CH3:3])[CH3:2].[CH3:16][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[C:20]=1[NH:28][C:29](=[O:44])[CH2:30][NH:31][CH2:32][C:33]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH3:18]>C(OCC)(=O)C>[CH3:18][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[C:20]=1[NH:28][C:29](=[O:44])[CH2:30][N:31]([C:14]([NH:13][C:5]1[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])=[O:15])[CH2:32][C:33]1([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH3:16]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 19874901HCID 19874901, compound

Product 1

HCID 19874880HCID 19874880, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,6-Diisopropylphenylisocyanate (0.24 g) and the product of Example 6 (0.45 g) were mixed and then diluted with a few mL of ethyl acetate. The solution was heated on the steambath and then concentrated to an oil which was heated on the steambath. Upon cooling to room temperature the oil partially solidified. Addition of hexane/EtoAc, 1/1 caused crystallization of the product which was collected by filtration. 0.30 g (44%). NMR (CDCl3) δ 1.08 (12H ,d), δ 1.17 (12H, d), δ 1.60-2.13 (8H, m), δ 2.65 (2H, m), δ 3.04 (2H, m), δ 3.71 (2H, s), δ 4.04 (2H, bs), δ 5.24 (1H, bs), δ 7.04-7.48 (11H, m), δ 7.94 (1H, bs). IR (KBr) 3025, 2965, 2871, 1682, 1637, 1519, 1364, 1230, 958, 801, 700 cm-1.

Workup

  1. temperatureThe solution was heated on the steambath
  2. concentrationconcentrated to an oil which
  3. temperaturewas heated on the steambath
  4. additionAddition of hexane/EtoAc, 1/1
  5. customcrystallization of the product which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c2df77139c9a41548c237531ed5fcd1f
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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