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

HRID 1626724노트

반응식

HRID 1626724 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7acbd7cfee14498ba6699438d4cfee51
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785473B2

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