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

HRID 716855ノート

反応式

HRID 716855 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3c9f5ff5b3d3441983c48a197a31561a
出典データセット
uspto-grants-2015_11
特許番号
US09193687B2

反応ノート

読み込み中…