3-Isocyanatobenzonitrile → HCID 57842786, compound

HRID 735606Notes

Reaction equation

HRID 735606 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=O)[O:11]CCC2C=CC(Br)=CC=2C)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:23][C:24]1[CH:29]=[C:28]([CH2:30][CH3:31])[C:27]([CH2:32][CH2:33][OH:34])=[C:26]([CH2:35][CH3:36])[CH:25]=1.N(C1C=C(C=CC=1)C#N)=C=O>>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:11])[O:34][CH2:33][CH2:32][C:27]2[C:26]([CH2:35][CH3:36])=[CH:25][C:24]([Br:23])=[CH:29][C:28]=2[CH2:30][CH3:31])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 3

HCID 27333153-IsocyanatobenzonitrileHCID 578428474-Bromo-2-methylphenethyl 3-cyanophenylcarbamateHCID 578429172-(4-Bromo-2,6-diethylphenyl)ethanol

Product 1

HCID 57842786HCID 57842786, compoundYield 86%

Procedure

Using a procedure analogous to that used to prepare 30C, 37C (280 mg, 1.95 mmol) was reacted with 3-isocyanatobenzonitrile to yield 37D (670 mg, 86%) as an yellow oil. 1H NMR (400 MHz, CD3OD) δ ppm 1.22 (t, J=7.58 Hz, 6 H) 2.73 (q, J=7.58 Hz, 4 H) 3.06 (t, J=8.1 Hz, 2 H) 4.21 (t, J=8.1 Hz, 2H) 7.19 (s, 2 H) 7.32-7.39 (m, 1 H) 7.40-7.50 (m, J=8.08, 8.08 Hz, 1 H) 7.66 (d, J=8.34 Hz, 1 H) 7.86 (s, 1 H).

Sources & evidence

ORD record
ord-eb5ca2644869409ab3fd33a11bae5fcc
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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