Hydrochloric Acid → 1,2,3-Benzothiadiazole

HRID 389464ノート

反応式

HRID 389464 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 675051,2,3-Benzothiadiazole収率 78.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-114b52cc74dc4c5688176447144648e9
出典データセット
uspto-grants-2013_02
特許番号
US08378104B2

反応ノート

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