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

HRID 732545Notes

Reaction equation

HRID 732545 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.O.ON1C2C=CC=CC=2N=N1.[CH:26]1([N:32]=[C:33]=NC2CCCCC2)CCC[CH2:28][CH2:27]1.CNCCC>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[C:11]([I:13])[CH:10]=[C:6]([C:7]([N:32]([CH3:33])[CH2:26][CH2:27][CH3:28])=[O:9])[CH:5]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12315N-MethylpropylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 5-iodo-isophthalic acid monomethyl ester (9.34 g, 30.5 mmol), 1-hydroxybenzotriazole hydrate (4.86 g, 36 mmol) and a solution of 1,3-dicyclohexylcarbodiimide (1 M in dichloromethane; 36 mL) in THF (70 mL). Cool to 0° C. for 15 min. Add methylpropylamine (3.69 mL, 36 mmol) and stir at room temperature for 12 h. Filter the solution though a filtering agent and wash with ethyl acetate, concentrate and purify (silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes) to give the title compound.

Workup

  1. filtrationFilter the solution though a filtering agent
  2. washwash with ethyl acetate
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-c6a494144e114ecf94c1eb4a6e9eeff2
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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