Methylamine → N-methyl-3-(4-nitrophenoxy)benzamide

HRID 78318

反応式

HRID 78318 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(O)=[O:2].C[CH2:21][N:22]=C=NCCCN(C)C.Cl.CN1CCOCC1.CN>C(Cl)Cl>[CH3:21][NH:22][C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:2]

参加物

6

反応物 4

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 7679193-(4-Nitrophenoxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 23614569N-methyl-3-(4-nitrophenoxy)benzamide収率 48.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCI.HCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0 M in THF; 8 mL, 16 mmol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2×50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. extractionthe resulting mixture was extracted with a 1M HCl solution (50 mL)
  4. extractionThe aqueous layer was back-extracted with EtOAc (2×50 mL)
  5. washThe combined organic phases were washed with a saturated NaCl solution (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0dd378f36dff4e6e9142dd23339d7922
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

関連ノート

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