Toluene → N,N-diethyl-2-methoxybenzamide

HRID 2427933Notes

Reaction equation

HRID 2427933 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([NH:10][CH2:11][CH3:12])[CH3:9].[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].Cl.C(NCC)C>O>[CH2:8]([N:10]([CH2:11][CH3:12])[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[O:14][CH3:13])[CH3:9]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 8021Diethylamine2×HCID 889692-Methoxybenzoyl chlorideHCID 10197650Diethylammonium chloride

Product 1

HCID 346975N,N-diethyl-2-methoxybenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a three-necked flask (200 ml), a toluene solution (56 g) containing diethylamine (25.80 g; 0.352 moles) was placed. While the flask was cooled with ice water and the solution was stirred, a toluene solution (30 g) of 2-methoxybenzoyl chloride (2.00 g; 0.117 moles) was added dropwise over 30 minutes. After the addition was completed, water was added to the resultant mixture, and diethylamine and diethylamine hydrochloride in excess amounts were removed. The obtained toluene layer was dehydrated with MgSO4. Then, the solvent was removed by distillation, and a light yellow liquid was obtained (the obtained amount: 22.81 g; the yield: 94%).

Workup

  1. additionAfter the addition
  2. customwere removed
  3. customThen, the solvent was removed by distillation
  4. customa light yellow liquid was obtained (the obtained amount

Sources & evidence

ORD record
ord-27c1a9d6f88e4ac38420f6416e184e57
Source dataset
uspto-grants-2011_06
Patent number
US07968751B2

Reaction notes

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