Triethylamine → Ethyl 3-bromo-5-[(4-chlorobutanoyl)amino]benzoate

HRID 269560Notes

Reaction equation

HRID 269560 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([Br:20])[CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:20][C:18]1[CH:17]=[C:11]([CH:10]=[C:9]([NH:8][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 63021768Ethyl 3-amino-5-bromobenzoate

Product 1

HCID 69312186Ethyl 3-bromo-5-[(4-chlorobutanoyl)amino]benzoateYield 94.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chlorobutyryl chloride (636 mg, 505 μl, 4.5 mmol) was added to a solution of ethyl 3-amino-5-bromobenzoate (1.0 g, 4.1 mmol) and triethylamine (455 mg, 630 ul, 4.5 mmol) in dichloromethane (25 ml) at 0° C. After complete addition the reaction mixture was stirred at room temperature for 30 minutes, then diluted with ethyl acetate (50 ml). The solution was washed with 2M HCl, saturated NaHCO3, water and brine. The organic phase was dried and evaporated to give the title compound as a pale yellow solid (1.35 g, 94%)

Workup

  1. additionAfter complete addition the reaction mixture
  2. washThe solution was washed with 2M HCl, saturated NaHCO3, water and brine
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-5ff5ffd25c704ae9a6213f879456d394
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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