2,6-Diisopropylphenyl isocyanate → HCID 18988273, compound

HRID 2396123Notes

Reaction equation

HRID 2396123 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][S:4]1.[CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[C:23]=1[N:31]=[C:32]=[O:33])([CH3:21])[CH3:20]>[Cl-]>[CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:29])[CH3:30])[C:23]=1[NH:31][C:32]([NH:1][CH2:2][CH:3]1[CH2:8][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][S:4]1)=[O:33])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 18988225HCID 18988225, compound

Product 1

HCID 18988273HCID 18988273, compound

Reagents, catalysts & solvents 1

HCID 312ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Part D. The amine product from Part C above (ca. 1.8 mmol) was dissolved inmethylene chloride (10 mL), and cooled to 0° C. The solution was treated with 2,6-diisopropylphenyl-isocyanate (0.50 mL, 2.10 mmol) by syringe. The mixture was allowed to stir for 12 hours, then evaporated, and the residue was separated by flash chromatography (7:93 ethyl acetate-hexane) to afford the title product as a solid, mp 65°-67° C. (490 mg, 1.04 mmol, 58%). 1H NMR (CDCl3): δ 7.40-7.07 (3H, m); 6.06 (1H, br s); 5.30 (1H, br s);3.61-3.46 (2H, m); 3.29 (2H, heptet, J=6.6 Hz); 3.19-2.87 (3H, m); 2.39-2.29 (1H, m); 2.08-1.96 (5H, m); 1.40-1.15 (24H, m); 0.88 (6H, t, J=6Hz); 0.87 (6H, t, J=6 Hz). 13C NMR (CDCl3): δ 157.9, 148.1, 131.1, 128.4, 128.0, 124.0, 123.4, 43.7, 40.0, 34.1, 33.9, 33.2, 32.0, 31.9, 28.6, 28.4, 28.3, 28.0, 25.6, 24.1, 23.9, 22.6, 14.1, 14.0. IR(KBr): 3320, 2960, 2928, 1638, 1590, 1556, 1466, 1362, 1256 cm-1. Massspectrum (NH3 -CI/DDIP): m/z 475 (10%); 474 (34%); 473 (100%); 381 (99%); 252 (2%). High-resolution mass spectrum: for C29H49N2OS, calculated 473.3566, measured 473.3566, difference 0 ppm.

Workup

  1. customevaporated
  2. customthe residue was separated by flash chromatography (7:93 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-28af449bd2d04aaab24887b5a9a28a13
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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