Sodium Nitrite → N-(4-chloro-3-hydrazinylbenzyl)-2,2,2-trifluoroacetamide

HRID 59417

반응식

HRID 59417 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[N:17]([O-])=O.[Na+].Cl[Sn]Cl.O>Cl>[Cl:16][C:15]1[CH:14]=[CH:13][C:4]([CH2:5][NH:6][C:7](=[O:12])[C:8]([F:9])([F:10])[F:11])=[CH:3][C:2]=1[NH:1][NH2:17]

참가 물질

5

반응물 3

HCID 23668193Sodium NitriteHCID 43835034Tin dichloride dihydrateHCID 90019301N-(3-amino-4-chlorobenzyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 90019135N-(4-chloro-3-hydrazinylbenzyl)-2,2,2-trifluoroacetamide수율 15,385.3%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

반응 조건

온도
2.5 °C

실험 절차

To a cold solution of N-(3-amino-4-chlorobenzyl)-2,2,2-trifluoroacetamide (0.500 g, 0.017 mmol) in 6N HCl (50.0 mL), aqueous solution of NaNO2 (1.29 g, 0.018 mmol) was added at 0° C. and the reaction mass was stirred at 0-5° C. for 30 min. The reaction mass was added to a solution of SnCl2.H2O (22.18 g, 0.98 mmol) in 6N HCl at 0-5° C. and further continued stirring for 5-6 h at same temperature. The reaction mass was cooled, basified and extracted with DCM. The organic layer was separated, dried and concentrated to afford 0.700 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 4.22 (br s, 2H), 4.29 (d, J=6.0 Hz, 2H), 6.42-6.67 (m, 2H), 7.14-7.16 (m, 2H), 9.98 (br s, 1H).

후처리

  1. stirringfurther continued stirring for 5-6 h at same temperature
  2. temperatureThe reaction mass was cooled
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8a2e6d709199414dbace4b7033dcced3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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