Methylamine → N-methyl-3-nitrobenzamide

HRID 497453

반응식

HRID 497453 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:13][NH2:14]>O1CCCC1.C(OCC)(=O)C>[CH3:13][NH:14][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

참가 물질

5

반응물 2

HCID 6329MethylamineHCID 8495Benzoyl chloride, 3-nitro-

생성물 1

HCID 221964N-methyl-3-nitrobenzamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

In a dry flask 3-nitrobenzoyl chloride (7.00 g, 37.7 mmol) was dissolved in tetrahydrofuran (300 mL) and methylamine (41.5 mL of a 2.0 M solution in tetrahydrofuran, 82.9 mmol) was added. The reaction mixture was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate (500 mL) and extracted with water three times (100 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The crude solid (6.38 g, 94%) was used with further purification. 1H NMR (300 MHz, CDCl3), δ: 8.84 (bs, 1H), 8.67 (m, 1H), 8.37 (dd, J=8, J′=2, 1H), 8.28 (d, J=7, 1H), 7.78 (dd, J=8, J′=7, 1H), 2.83 (m, 3H). MS (ESI), m+/z: (M+H)+=181.

후처리

  1. extractionextracted with water three times (100 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude solid (6.38 g, 94%) was used with further purification

출처 및 근거

ORD 기록
ord-e232027aac894c56aa40fac6a94afe50
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949546B2

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