Diethylamine → 3-benzyloxy-N,N-diethyl-4-methoxy-benzamide

HRID 2297437Notes

Reaction equation

HRID 2297437 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:12](Cl)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:12]([N:22]([CH2:23][CH3:24])[CH2:20][CH3:21])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 109677953-Benzyloxy-4-methoxybenzoyl chloride

Product 1

HCID 185048043-benzyloxy-N,N-diethyl-4-methoxy-benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-benzyloxy-4-methoxy-benzoyl chloride (35.01 g, 0.127 mole), prepared as described in example 54, in CH2Cl2 (200 ml) was dropwise added at 5-10° C. with diethylamine (131 ml, 92.54 g, 1.27 mole) in CH2Cl2 (130 ml). The mixture was evaporated to dryness, dissolved in ethyl acetate, washed with water, 2% KHSO4, water again and NaHCO3, anhydrified over Na2SO4 and brought to dryness. The residue was taken up in petrolatum (250 ml) to give 37.65 g of the title compound (yield: 95%)

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water, 2% KHSO4, water again

Sources & evidence

ORD record
ord-785878f5ceff4e1fa6bf66973e20f5aa
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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