N-Methylaniline → N-phenyl-N-methyl-2-benzyloxy-5-formylbenzamide

HRID 1583027Notes

Reaction equation

HRID 1583027 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]([O:16][C:17]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][C:18]=1[C:19]([OH:21])=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:3]1([N:2]([CH3:1])[C:19](=[O:21])[C:18]2[CH:22]=[C:23]([CH:26]=[O:27])[CH:24]=[CH:25][C:17]=2[O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 7515N-MethylanilineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 9698702-(Benzyloxy)-5-formylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22716821N-phenyl-N-methyl-2-benzyloxy-5-formylbenzamideYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methylaniline (0.18 mL, 1.68 mmol, 2 eq) was added to a solution of 2-benzyloxy-5-formylbenzoic acid (200 mg, 0.84 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (230 mg, 1.68 mmol, 2 eq), and N-methylmorpholine (0.25 mL, 2.29 mmol, 2.73 eq) in N,N-dimethylformamide (4 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (320 mg, 1.68 mmol, 2 eq) and the reaction mixture stirred overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a yellow oil (270 mg, 99%). RF (petroleum ether:ethyl acetate 1:1) 0.73. 1H NMR (CDCl3) δ9.79 (s, 1H, O═C—H), 5.01 (s, 2H, CH2Ph), 3.47 (s, 3H, CH3).

Workup

  1. washwashed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f9f190d5fd02432da3adf89f283d09c4
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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