Triethylamine → 3-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[CH:6]=1.CCN(CC)CC.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH:13][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][Cl:22])[CH:6]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (0.13 g, 0.556 mmol, 1 equiv) in dry CH2Cl2 (2 ml) at 0° C. was added NEt3 (193 ml, 1.39 mmol, 2.5 equiv) then 4-chlorobutyryl chloride (69 ml, 0.612 mmol, 1.1 equiv), dropwise, over 2 min. The resulting solution was stirred at 0° C. for 15 min then at room temperature for 30 min. The solution was then diluted with AcOEt, washed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give 3-(4-chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester (D64) (173 mg, 103%) as pale yellow crystals. [M+H]+=302.0, RT=3.20 min
Workup
- waitat room temperature for 30 min
- washwashed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6ed46d440efe4513ae9c5a11f1d3fda9
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253198B2
Reaction notes
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