Stannous Chloride → HCID 10265481, 화합물

HRID 1824587노트

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HRID 1824587 반응식
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[N+:19]([O-])=O)[CH3:3].Cl[Sn]Cl>CO.Cl>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH2:19])[CH3:1]

참가 물질

5

반응물 2

HCID 24479Stannous ChlorideHCID 11415526HCID 11415526, 화합물

생성물 1

HCID 10265481HCID 10265481, 화합물수율 42.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

To a yellow solution of compound 10 (200 mg, 0.65 mmol) in CH3OH (4 mL) and conc. HCl (2 mL), SnCl2 (0–3 g) was added. The mixture was stirred at room temperature overnight and the solvent was evaporated to dryness. Water (15 mL) was added to the residue and the mixture was extracted with ethyl acetate (10 mL×3). The organic layer was discarded and the aqueous layer was adjusted to pH 10 with 1 N NaOH. The cloudy solution was extracted with ethyl acetate (10 mL×3). The combined organic layer was dried over Na2SO4 and the solvent was evaporated in vacuo to dryness. The residue was purified by column chromatography (silica gel, CH2Cl2/CH3OH, 95/5) to yield compound 12 as a white solid (77 mg, 42.7%), Rf=0.3 (silica gel, CH2Cl2/CH3OH, 90/10), mp 56–58° C.; 1H NMR (CDCl3) δ 7.40–7.49 (m, 1H), 7.18–7.25 (m, 1H), 7.05–7.13 (m, 2H), 6.84–6.93) (m, 1H), 6.38–6.48 (m, 2H), 4.74 (s, b, 2H), 3.57 (s, 2H), 2.31 (s, 6H). Anal. Calcd for C15H17FN2S: C, 65.19; H, 6.20; N, 10.14. Found: C, 65.06; H, 6.23; N, 10.04.

후처리

  1. customthe solvent was evaporated to dryness
  2. additionWater (15 mL) was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (10 mL×3)
  4. extractionThe cloudy solution was extracted with ethyl acetate (10 mL×3)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. customthe solvent was evaporated in vacuo to dryness
  7. customThe residue was purified by column chromatography (silica gel, CH2Cl2/CH3OH, 95/5)

출처 및 근거

ORD 기록
ord-11155cdc6475404dbdf6ee898d177006
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041851B2

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