Triethylamine → HCID 67352936, compound

HRID 1669980Notes

Reaction equation

HRID 1669980 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10].[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Br:22])[C:16](Cl)=[O:17].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:21]([Br:22])=[C:13]([CH3:12])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 70215344-Bromo-3-methylbenzoyl chloride

Product 1

HCID 67352936HCID 67352936, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-amino-benzoic acid methyl ester (3.1 g) in dichloromethane (31 mL) under slight cooling was added 3-methyl-4-bromobenzoyl chloride ([21900-25-4], 4.8 g) followed by a triethylamine (3.15 mL). The temperature of the solution was kept below 40° C. and the reaction mixture was then stirred at room temperature for an hour. After such time, additional dichloromethane was added (50 mL) and the reaction mixture was washed with water. The aqueous phase was further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (heptane-ethyl acetate: 0-50%) to yield 2-(4-bromo-3-methyl-benzoylamino)-benzoic acid methyl ester (7.1 g). MS (m/e): 348.3 (M+H+, 100%).

Workup

  1. customwas kept below 40° C.
  2. washthe reaction mixture was washed with water
  3. extractionThe aqueous phase was further extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (heptane-ethyl acetate: 0-50%)

Sources & evidence

ORD record
ord-9a6357187e1445a391df88b345156a6b
Source dataset
uspto-grants-2011_08
Patent number
US07989657B2

Reaction notes

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