Hydrochloric Acid → Benzothiazolone

HRID 2246747Notes

Reaction equation

HRID 2246747 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10].Cl>C1COCC1>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:9]1=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 87132-AminothiophenolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 13625Benzothiazolone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-benzenethiol (10 g, 79.9 mmol) in THF (200 mL) at room temperature was added carbonyldiimidazole (14.3 g, 87.9 mmol) and the reaction solution stirred for 12 hours. Upon disappearance of starting material, the reaction solution was poured into 1N HCl (125 mL) and extracted with ethyl acetate (125 mL). The organic layer was dried over sodium sulfate and concentrated to give 1,3-benzothiazol-2(3H)-one as a white solid. MS (ES) m/z 152.1.

Workup

  1. extractionextracted with ethyl acetate (125 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-90f243a22e6b425a90fc5a746f0d1749
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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