Dimethylamine → 3-(dimethylamino)-N-(3-nitrophenyl)propanamide

HRID 716855노트

반응식

HRID 716855 반응식
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=[O:5].[CH3:16][NH:17][CH3:18]>C1COCC1>[CH3:16][N:17]([CH3:18])[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=[O:5]

참가 물질

4

반응물 2

HCID 674DimethylamineHCID 34652363-chloro-N-(3-nitrophenyl)propanamide

생성물 1

HCID 866899623-(dimethylamino)-N-(3-nitrophenyl)propanamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-chloro-N-(3-nitrophenyl)propanamide (4.6 g, 20 mmol) in THF (50 mL) was added dropwise N,N-dimethyl amine (2M solution in THF) (1.8 g, 20 mL, 40 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was triturated with 5% NH3 (aqueous, 50 mL) and the solid product was collected by filtration, washed with water followed by hexane, and dried to give 3-(dimethylamino)-N-(3-nitrophenyl)propanamide, 4.1 g (87%), mp 80-81° C. 1H NMR (DMSO-d6) δ: 2.17 (6H, s, CH3), 2.47-2.50 (2H, t, J=6.4 Hz, CH), 2.56-2.59 (2H, t, J=6.8 Hz, CH), 7.57-7.62 (1H, t, J=8.2 Hz, Ar—H), 7.88-7.91 (2H, dd, J=8.1 and 2.2 Hz, Ar—H), 8.63-8.64 (1H, t, J=2.0 Hz, Ar—H), 10.49 (1H, brs, NH).

후처리

  1. customevaporated to dryness under reduced pressure
  2. customThe residue was triturated with 5% NH3 (aqueous, 50 mL)
  3. filtrationthe solid product was collected by filtration
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-3c9f5ff5b3d3441983c48a197a31561a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193687B2

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