Aniline → 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamide

HRID 505651Notes

Reaction equation

HRID 505651 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1.ClCCl>[CH2:1]([O:8][CH2:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 687174092-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid

Product 1

HCID 687177352-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamideYield 476.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (35 mg, 0.0096 mmol) obtained in Step 6 of Example 22 was dissolved in tetrahydrofuran (4 mL) and dichloromethane (1 mL), and aniline (0.030 mL, 0.33 mmol), 1-hydroxybenzotriazole monohydrate (56 mg, 0.37 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.13 g, 0.68 mmol) were added to the obtained solution followed by stirring at a room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=100/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamide (20 mg, 49%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-dc331662a0ba46979373d5077013fa4a
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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