1,2-Dichloroethane → 4,5-difluoro-N-methyl-2-nitrobenzamide

HRID 1887698노트

반응식

HRID 1887698 반응식
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:28][CH3:26])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 42196304,5-Difluoro-2-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

생성물 1

HCID 619939344,5-difluoro-N-methyl-2-nitrobenzamide수율 67%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4,5-difluoro-2-nitrobenzoic acid (1.872 g, 9.22 mmol), methylamine hydrogen chloride (0.75 g, 1.2 eq), EDC (2.12 g, 1.2 eq), HOBt (1.5 g, 1.2 eq) in DMF (20 mL) was added DIEA (5.0 mL, 3.0 eq). The mixture was stirred at room temperature for 15 min. It was concentrated and the crude was dissolved in EtOAc. It was washed with a saturated NaHCO3. The solvent was removed and the crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex) to obtain the desired product 4,5-difluoro-N-methyl-2-nitrobenzamide (1.33 g, isolated yield 67%).

후처리

  1. concentrationIt was concentrated
  2. dissolutionthe crude was dissolved in EtOAc
  3. washIt was washed with a saturated NaHCO3
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-fd3f9e7265604aed877b91aafb4e3ad3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501763B2

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