4-Methoxybenzyl alcohol → HCID 22226607, compound

HRID 1745851Notes

Reaction equation

HRID 1745851 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]O)=[CH:27][CH:26]=1>C(#N)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 800192-Amino-5-chlorobenzonitrileHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22226607HCID 22226607, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 2-amino-5-chlorobenzonitrile (0.50 g, 3.28 mmol) in 2 mL of acetonitrile was treated with p-toluenesulfonic acid monohydrate. The reaction mixture was heated to 70° C. with stirring. 4-Methoxybenzyl alcohol (0.50, 3.61 mmol) in acetonitrile (1 mL) was added dropwise via syringe keeping the reaction temperature at 70° C. The reaction was stirred at 70° C. for 12 h, allowed to cool to ambient temperature, and concentrated in vacuo. Chromatography afforded 1 (0.884 g, 99%) as light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.36 (d, J=2.4 Hz, 1H), 7.27 (dd, J=9 Hz, 1H), 7.24 (d, J=8.6 Hz, 2H), 6.89 (d, J=8.6 Hz, 2H), 6.58 (d, J=9 Hz, 1H), 4.95 (br S, 1H), 4.33 (d, J=5.4 Hz, 2H), 3.81 (s, 3H).

Workup

  1. customat 70° C
  2. stirringThe reaction was stirred at 70° C. for 12 h
  3. temperatureto cool to ambient temperature
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-422907e9ffe04648ab6ce2dbefb7763d
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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