4-Aminobenzoic Acid → 4-(2-Chlorobenzamido)benzoic acid

HRID 1951597노트

반응식

HRID 1951597 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].C(N(CC)CC)C>C(#N)C>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:15]

참가 물질

5

반응물 3

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chloride

생성물 1

HCID 11329884-(2-Chlorobenzamido)benzoic acid수율 54.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

under an N2 atmosphere, 4-aminobenzoic acid (2.50 g, 18.2 mmol) was dissolved in acetonitrile (100 ml) and treated with 2-chlorobenzoyl chloride (2.43 ml, 19.1 mmol). Triethylamine (2.66 ml, 19.1 mmol) was added and the reaction was allowed to stir at room temperature for four hours. The reaction was concentrated in vacuo, and the resulting solid was partitioned between Et2O and 0.5N NaOH. The layers were separated and the organic layer was discarded. The aqueous layer was acidified to pH 2 with HCl and the aqueous layer was extracted with ethyl acetate. The organic layer was dried Na2SO4, filtered and concentrated in vacuo. The resulting solid was triturated with Et2O, and the solid was collected by filtration to afford 4-(2-chlorobenzamido)benzoic acid (2.72 g, 54.2% yield). ESI m/z=276.1 (M+H+).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting solid was partitioned between Et2O and 0.5N NaOH
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was triturated with Et2O
  8. filtrationthe solid was collected by filtration

출처 및 근거

ORD 기록
ord-f7828a428a6740bfaeb3b3fecd1c9803
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404722B2

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