Hydrochloric Acid → 2-[(3-phenoxybenzyl)thio]-5,6-dihydro-1,3-benzothiazol-7(4H)-one

HRID 1163309Notes

Reaction equation

HRID 1163309 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C:17]([NH2:19])=[S:18].[OH-].[Na+].ClC1[S:24][C:25]2[C:31](=[O:32])[CH2:30][CH2:29][CH2:28][C:26]=2N=1.Cl>C(O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][S:18][C:17]1[S:24][C:25]2[C:31](=[O:32])[CH2:30][CH2:29][CH2:28][C:26]=2[N:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 932913-Phenoxybenzyl chlorideHCID 5942872-Chloro-5,6-dihydro-4H-benzothiazol-7-oneHCID 2723790Thiourea

Product 1

HCID 231118532-[(3-phenoxybenzyl)thio]-5,6-dihydro-1,3-benzothiazol-7(4H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-phenoxybenzyl chloride (2.84 g, 13.0 mmol), thiourea (1.22 g, 16 mmol) and ethanol (30 mL) was heated under reflux for 1 hr. 1 M aqueous sodium hydroxide solution (20 mL) was added to the reaction mixture and the mixture was further heated under reflux for 1 hr. The reaction mixture was cooled, and 2-chloro-5,6-dihydro-1,3-benzothiazol-7(4H)-one (1.55 g, 7.99 mmol) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (AcOEt:hexane=1:19-1:1) to give the title compound (2.67 g, yield 91%) as a pale-yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 1 hr
  5. temperatureThe reaction mixture was cooled
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed successively with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (AcOEt:hexane=1:19-1:1)

Sources & evidence

ORD record
ord-32655c6c3d39426881af7fbb4e1b2135
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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