HCID 303421, compound → 2H-1-Benzopyran-2-thione (9CI)

HRID 378172Notes

Reaction equation

HRID 378172 reaction equation
[C:1]([S:11]C1C=CC=CC=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[O:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2][C:1]1=[S:11]

Participants

3

Reactant 2

HCID 303421HCID 303421, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 198902H-1-Benzopyran-2-thione (9CI)Yield 55%

Conditions

Temperature
85 °C

Procedure

A mixture of S-phenyl thiocinnamate (14.0 g, 58.25 mmol) and aluminum chloride (39 g) was stirred and heated at 85° C. for 3 hours. The hot reaction mixture was poured carefully over ice, then was extracted with ethyl acetate (3×300 mL), washed with brine (200 mL), dried (MgSO4) and was concentrated. The residue was recrystallized from hexane-ethyl acetate to afford 5.2 g (52%) of the desired product as pale yellow crystals.

Workup

  1. additionThe hot reaction mixture was poured carefully over ice
  2. extractionwas extracted with ethyl acetate (3×300 mL)
  3. washwashed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationwas concentrated
  6. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8c2bd3e0a21c442288e773e596f2e198
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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