Triethylamine → HCID 67352936, compound

HRID 1669975Notes

Reaction equation

HRID 1669975 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].[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][C:14]=1[CH3:22].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:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[C:14]([CH3:22])[CH:15]=1

Participants

5

Reactant 3

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

Product 1

HCID 67352936HCID 67352936, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-amino-benzoic acid methyl ester (3.1 g) in dichloromethane (31 mL) was slowly added 4-bromo-3-methyl-benzoyl chloride [21900-25-4] (4.8 g) and triethylamine (3.1 mL). The reaction mixture was then stirred at room temperature for 1 hour. After such time, the reaction mixture was further diluted with dichloromethane (50 mL) and washed with water. The combined aqueous phase was further extracted with dichloromethane. All combined organic phases were then dried over sodium sulfate and concentrated in vacuo. The residue was then recrystallised from ethanol to give 2-(4-bromo-3-methyl-benzoylamino)-benzoic acid methyl ester (6.14 g) as white crystals, m.p.=123° C. MS (m/e): 348.3 (M+H+, 100%).

Workup

  1. washwashed with water
  2. extractionThe combined aqueous phase was further extracted with dichloromethane
  3. dry with materialwere then dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was then recrystallised from ethanol

Sources & evidence

ORD record
ord-ea2e344171e548e18370f1612686ea6a
Source dataset
uspto-grants-2011_08
Patent number
US07989657B2

Reaction notes

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