N-Methylpropylamine → Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

HRID 732534

Reaction equation

HRID 732534 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[C:11]([I:13])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.[CH3:15][NH:16][CH2:17][CH2:18][CH3:19].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[C:11]([I:13])[CH:10]=[C:6]([C:7]([N:16]([CH3:15])[CH2:17][CH2:18][CH3:19])=[O:9])[CH:5]=1

Participants

6

Reactant 4

HCID 12315N-MethylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoateYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mix 5-iodo-isophthalic acid monomethyl ester (3.6 g), N-methyl propyl amine (1.2 mL, 11.8 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.3 g, 11.8 mmol), and 1-hydroxybenzotriazole hydrate (1.6 g, 11.8 mmol) in dichloromethane (40 mL) and stir at room temperature for 4 h. Dilute with dichloromethane (20 mL), wash with water, 5% aqueous ammonium chloride solution, 5% aqueous sodium bicarbonate solution. Dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (3.2 g, 74%).

Workup

  1. washwash with water, 5% aqueous ammonium chloride solution, 5% aqueous sodium bicarbonate solution
  2. dry with materialDry (sodium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-2ae68db5ccde4037ab94d90d82891dce
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Linked notes

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