1,2-Dichloroethane → 3-[2-(2,4,5-Trichloro-phenoxy)acetyl-amino]-benzamide

HRID 1945385

반응식

HRID 1945385 반응식
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20])=[O:8]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 1480Trichlorophenoxyacetic acidHCID 16453-AminobenzamideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

생성물 1

HCID 248111053-[2-(2,4,5-Trichloro-phenoxy)acetyl-amino]-benzamide수율 84.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the 2,4,5-trichloro-phenoxy acetic acid (76.7 mg, 0.3 mmol), 3-amino benzamide (61.3 mg, 0.45 mmol), EDC (86.3 mg, 0.45 mmol) and HOBt (61.3 mg, 0.45 mmol) were dissolved in DMF (3 mL), and DIPEA (0.08 mL, 0.45 mmol) were added. The reaction mixture was stirred at room temperature overnight, and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (CH2Cl2:MeOH=6:3:1) gave 3-[2-(2,4,5-trichloro-phenoxy)acetyl-amino]-benzamide as a white solid (95.2 mg, 84.9% yield).

후처리

  1. custompartitioned between Ethyl acetate and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (CH2Cl2:MeOH=6:3:1)

출처 및 근거

ORD 기록
ord-1638c6b9dae34265b2de453734b00d69
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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