Hydrochloric Acid → 1,2,3-Benzothiadiazole

HRID 389464Notes

Reaction equation

HRID 389464 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 675051,2,3-BenzothiadiazoleYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-114b52cc74dc4c5688176447144648e9
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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