1,2-Dichloroethane → 2',3'-Dimethyl-3-nitrobenzanilide

HRID 1780803

반응식

HRID 1780803 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:13][C:14]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].ON1C2C=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:14]=1[CH3:13])=[O:9])([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 68932,3-DimethylanilineHCID 84973-Nitrobenzoic acidHCID 757711-Hydroxybenzotriazole

생성물 1

HCID 8165712',3'-Dimethyl-3-nitrobenzanilide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 3-nitrobenzoic acid (3.0 g ) and 2,3-dimethylaniline (2.17 g) in 20 mL of DMF was added 1-hydroxybenzotriazole (2.75 g), EDC (3.44 g) and triethylamine (7.39 mL). The resulting solution was stirred for 16 h. The DMF was evaporated in vacuo and the residue was partitioned with ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid. NMR (300 MHz, CDCl3) δ 8.72 (1H, s), 8.40 (1 H, d, J=6 Hz), 8.26 (1H, d, J=9 Hz), 7.93 (IH, s), 7.69 (1H, t, J=9 Hz), 7.45 (1 H,d, J=9 Hz), 7.14 (1H, t, J=8 Hz), 7.08 (1H, d, J=9 Hz), 2.32 (3H, s), 2.21 (3H, s).

후처리

  1. customThe DMF was evaporated in vacuo
  2. customthe residue was partitioned with ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4a7c0436fc1c4910b757badd95221d5b
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631280

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