Triethylamine → HCID 86677590, compound

HRID 1397259Notes

Reaction equation

HRID 1397259 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].CCN(CC)CC.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:22]=1)[C:17]([OH:19])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Br:13][C:14]1[CH:22]=[C:21]([CH:20]=[C:16]([C:17](=[O:19])[N:3]([O:4][CH3:5])[CH3:2])[CH:15]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 86677590HCID 86677590, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine hydrochloride (1.15 g, 11.8 mmol) was dissolved in CH2Cl2 (50 mL) and Et3N (4.8 mL, 34.4 mmol) was added. The solution was stirred for 30 min. The resultant solution was cooled to 0° C. and compound 3-bromo-5-(methoxycarbonyl)benzoic acid (2.55 g, 9.84 mmol) was added followed by EDC.HCl (3.77 g, 19.6 mmol) and HOBt (0.26 g, 1.96 mmol). The reaction mixture was allowed to come to room temperature and stirred for another 4 h. After completion, the reaction mixture was diluted with CH2Cl2. The organic layer was washed with water and brine solution and dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica 60-120 mesh, eluent 20% EtOAc in petroleum ether) to get methyl 3-bromo-5-(methoxy(methyl)carbamoyl)benzoate (2.3 g, yield 77%) as colorless liquid. 1H NMR (400 MHz, CDCl3) δ 8.29 (m, 1H), 8.27 (t, J=1.8 Hz, 1H), 8.02 (t, J=1.6 Hz, 1H), 3.95 (s, 3H), 3.57 (s, 3H), 3.39 (s, 3H). MS (ESI) m/z: Calculated for C11H12BrNO4: 300.99. found: 302.0 (M+H)+.

Workup

  1. customto come to room temperature
  2. stirringstirred for another 4 h
  3. washThe organic layer was washed with water and brine solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography (silica 60-120 mesh, eluent 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fcd4583c789d4e349340b4f31ac32f9a
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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