Potassium Carbonate → Methyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate

HRID 1192074

반응식

HRID 1192074 반응식
[Na].[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[SH:9].Cl[C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[S:9][C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylateHCID 178527724HCID 178527724, 화합물

생성물 1

HCID 46932421Methyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate수율 23%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

3,5-dichloropyridine-4-thiol sodium salt prepared as in example 17 (0.179 g, 1 mmol), methyl 5-chloro-4-nitro-thiophene-2-carboxylate (221 mg, 1 mmol) was mixed in toluene (5 mL). Then potassium carbonate (0.207 g, 1.5 mmol) was added. The resulting reaction mixture was stirred at ambient temperature for 4 hours. After this time, the reaction mixture was filtered and diluted with ethyl acetate. The organic solution was washed with water (2 mL×2), brine (2 mL×2), dried (Na2SO4), and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with a 96:4 mixture of hexane and ethyl acetate to afford the title product as a solid (82.5 mg, 23% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.05 (2H, s), 8.20 (1H, s), 3.82 (3H, s). MS m/z: 365.2 [M+H]+.

후처리

  1. customThe resulting reaction mixture
  2. filtrationAfter this time, the reaction mixture was filtered
  3. additiondiluted with ethyl acetate
  4. washThe organic solution was washed with water (2 mL×2), brine (2 mL×2)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a 96:4 mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-db302e0579fb4d968464959adf3813fc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680139B2

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