Sodium Carbonate → 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one

HRID 1962

반응식

HRID 1962 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH2:19][CH2:20][CH:21]=[CH2:22])=[N:14]1.C(=O)([O-])[O-:24].[Na+].[Na+].ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH2:19][CH2:20][CH:21]2[O:24][CH2:22]2)=[N:14]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 1359741252-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one

생성물 1

HCID 1360548852-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one수율 95.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 500 mg (1.48 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3-butenyl)-3H- 1,2,4-triazol-3-one in 20 mL of dichloromethane was added 172 mg (1.63 mmol) of sodium carbonate and 970 mg of m-chloroperoxybenzoic acid (50-60%, 2.81 mmol) in an ice bath. The reaction mixture was stirred at room temperature for 24h. The mixture was filtered and the filtrate was evaporated in vacuo to give 500 mg of the title compound of Step 3 as yellow solid. The crude product was used in the following reaction without further purification. 1H NMR (CDCl3, 400 MHz) δ 11.25 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 4.8 (s,2H), 3.05 (m,1H), 2.8 (t,1H), 2.8 (t,2H), 2.6 (s,1H), 2.75 (d,1H), 2.2 (m,1H), 1.8 (m,1H).

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-c4fd97650ffa477c91c1528e59316f4a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728651

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