4-Methoxybenzyl alcohol → 5-chloro-N-methoxy-2-(4-methoxy-benzylamino)-N-methyl-benzamide

HRID 1745856Notes

Reaction equation

HRID 1745856 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]O)=[CH:31][CH:30]=1>C(#N)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:2]([NH:1][CH2:33][C:32]2[CH:35]=[CH:36][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[C:3]([CH:10]=1)[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamide

Product 1

HCID 222266005-chloro-N-methoxy-2-(4-methoxy-benzylamino)-N-methyl-benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 8 (3.75 g, 17.3 mmol) in 50 mL of acetonitrile was treated with p-toluenesulfonic acid monohydrate. The reaction mixture was heated to 70° C. with stirring. 4-Methoxybenzyl alcohol (2.63 g, 19.0 mmol) in acetonitrile (3 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 9 (4.3 g, 75%) as light yellow solid.

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-8d7eb74964664e4ba7a9404a316a2cec
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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