Hydrochloric Acid → 1,2,3-Benzothiadiazole

HRID 389464

반응식

HRID 389464 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl.[N:10]([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C1COCC1>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[N:10]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 23668193Sodium Nitrite

생성물 1

HCID 675051,2,3-Benzothiadiazole수율 78.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 2-aminobenzenethiol (1.00 g, 7.99 mmol) in water (8 mL) was added aqueous 12 N hydrochloric acid (2 mL, 20 mmol) slowly at rt. Sodium nitrite (827 mg, 12.0 mmol) was then added slowly at rt. THF (4 mL) was added for solubility, and the reaction was stirred at rt for 30 min. The solution was neutralized with saturated aqueous potassium carbonate, and the material was extracted with DCM and saturated aqueous sodium bicarbonate. The organic layer was purified via column chromatography (1% EtOAc:heptane) to afford 850 mg (78%) of the title compound as an orange liquid. 1H NMR (400 MHz, CDCl3): δ 7.63-7.73 (m, 2 H), 8.12 (dt, J=8.3, 0.9 Hz, 1 H), 8.66 (dt, J=8.5, 0.9 Hz, 1 H).

후처리

  1. extractionthe material was extracted with DCM and saturated aqueous sodium bicarbonate
  2. customThe organic layer was purified via column chromatography (1% EtOAc:heptane)

출처 및 근거

ORD 기록
ord-114b52cc74dc4c5688176447144648e9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

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