Oxalyl chloride → Methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate

HRID 1626724ノート

反応式

HRID 1626724 の反応式
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.[NH2:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])O.[Na+]>C1COCC1.CC(N(C)C)=O.CN(C)C=O>[Cl:32][C:29]1[CH:30]=[CH:31][C:22]([NH:21][C:9]([C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[CH:7]=2)=[O:11])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25]

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 516892Sodium BicarbonateHCID 189451333-(Furan-3-yl)benzoic acid

生成物 1

HCID 66680385Methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate収率 67%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 31374Dimethylacetamide溶媒

実験手順

0.50 g (2.7 mmol) of 3-(furan-3-yl)benzoic acid, a catalytic amount of N,N-dimethylformamide (DMF), 0.78 g (3.7 mmol) of oxalyl chloride were stirred at 0° C. for 30 minutes in 10 mL of THF. Thereafter, the solvent was distilled off under reduced pressure. 0.49 g (2.7 mmol) of methyl 2-amino-5-chlorobenzoate and 5 mL of DMAc were added to the obtained residue at 0° C., and the mixture was stirred at room temperature for 0.5 hours. After the completion of the reaction, an aqueous sodium hydrogen carbonate solution was added. The precipitated solids were collected by filtration, followed by washing with water and IPE, thereby giving 0.63 g of methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate (yield: 67%).

後処理

  1. distillationThereafter, the solvent was distilled off under reduced pressure
  2. customAfter the completion of the reaction
  3. filtrationThe precipitated solids were collected by filtration
  4. washby washing with water and IPE

出典と根拠

ORDレコード
ord-7acbd7cfee14498ba6699438d4cfee51
出典データセット
uspto-grants-2014_07
特許番号
US08785473B2

反応ノート

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