Hydrochloric Acid → Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate

HRID 1436632

Reaction equation

HRID 1436632 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH3:5].[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[C:11]([C:12]([OH:14])=O)[CH:10]=1.BrC1C=C(C(O)=O)C=C(C=1)C(O)=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl-].[NH4+].Cl>ClCCl>[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[C:11]([C:12]([N:2]([CH3:1])[CH2:3][CH2:4][CH3:5])=[O:14])[CH:10]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 12315N-MethylpropylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 900735-Bromoisophthalic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 57529325Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoateYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add N-methylpropylamine (5.14 g, 70.4 mmol) to a mixture of 5-bromo-isophthalic acid monomethyl ester and 5-bromo-isophthalic acid (18.2 g), 1-hydroxybenzotriazole (9.5 g, 70.4 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.5 g, 70.4 mmol) in dichloromethane (200 mL). Stir the solution for 2 h at room temperature. Add saturated aqueous ammonium chloride (100 mL) and acidify the mixture with 1 N HCl. Filter away the precipitate, extract the filtrate with dichloromethane, wash the organic extracts with 1 N HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound as an oil (10.1 g, 46%).

Workup

  1. filtrationFilter away the precipitate
  2. extractionextract the filtrate with dichloromethane
  3. washwash the organic extracts with 1 N HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b4a49b99652d405b815196d3ea594cff
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Linked notes

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