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

HRID 1250857

Reaction equation

HRID 1250857 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 109677953-Benzyloxy-4-methoxybenzoyl chloride

Product 1

HCID 185048043-benzyloxy-N,N-diethyl-4-methoxy-benzamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diethylamine (548 ml, 5.3 moles) in CH2Cl2 (452 ml) was added dropwise to a solution of 3-benzyloxy-4-methoxy-benzoyl chloride (146.66 g, 0.53 moles), obtained as described in example 30, in methylene chloride (640 ml), at 0° C. under nitrogen, at constant temperature. At the end the temperature was left to arise to the room value. After 2 hours the mixture was evaporated, taken up with ethyl acetate and washed with water. The organic phase was dried and concentrated to give a solid which, triturated twice with heptane and once with petrolatum, then dried at 45° C. under vacuum gave 150.62 g of the title compound (yield: 91%).

Workup

  1. customobtained
  2. waitAt the end the temperature was left
  3. customAfter 2 hours the mixture was evaporated
  4. washwashed with water
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto give a solid which
  8. customtriturated twice with heptane and once with petrolatum
  9. customdried at 45° C. under vacuum

Sources & evidence

ORD record
ord-d18cfc26bba84e66a2d0e0bc4972c7c4
Source dataset
uspto-grants-2002_01
Patent number
US06340684B1

Linked notes

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