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

HRID 1887698ノート

反応式

HRID 1887698 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 619939344,5-difluoro-N-methyl-2-nitrobenzamide収率 67%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fd3f9e7265604aed877b91aafb4e3ad3
出典データセット
uspto-grants-2013_08
特許番号
US08501763B2

反応ノート

読み込み中…