Hydrochloric Acid → HCID 12767925, compound

HRID 1902243Notes

Reaction equation

HRID 1902243 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([SH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH:15]1[CH2:20][CH2:19][O:18][C:16]1=[O:17].Cl>O.C(OC(=O)C)(=O)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:15]3([C:9](=[O:11])[C:8]=2[CH:12]=1)[CH2:20][CH2:19][O:18][C:16]3=[O:17])([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 136222725-Nitro-2-sulfanylbenzoic acid

Product 1

HCID 12767925HCID 12767925, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolventHCID 8471TriethylamineSolvent

Procedure

In 200 ml of water was dissolved 4.45 g of dipotassium salt of 5-nitrothiosalicylic acid, and 3.55 g of α-bromo-γ-butyrolactone was added dropwise to the solution under ice-cooling with stirring. After stirring the solution at room temperature for 3.5 hours, 10 ml of concentrated hydrochloric acid was added to the solution to acidify, and the solution was subjected to extraction with ethyl acetate. The extract was washed with water, dried and evaporated to dryness under reduced pressure, resulting in α-[(2-carboxy-4-nitrophenyl)thio]-γ-butyrolactone. The crude product was dissolved in 50 ml of acetic anhydride and 10 ml of triethylamine, and heated under a stream of nitrogen at 130° C. for 30 minutes. The reaction solution was evaporated to dryness under reduced pressure, and the residue was chromatographed on a column of activated carbon and silica gel. Recrystallization from ethanol of the resultant crude crystals yielded pale yellow needles of 5-nitro-4',5'-dihydrospiro[benzo[b]thiophene-2(3H),3'(2'H)-furan]-3,2' -dione. Melting point: 190.5°-193.5° C.

Workup

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling
  3. stirringAfter stirring the solution at room temperature for 3.5 hours
  4. extractionthe solution was subjected to extraction with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customresulting in α-[(2-carboxy-4-nitrophenyl)thio]-γ-butyrolactone
  9. customThe reaction solution was evaporated to dryness under reduced pressure
  10. customthe residue was chromatographed on a column of activated carbon and silica gel
  11. customRecrystallization from ethanol of the resultant crude crystals

Sources & evidence

ORD record
ord-ab8ead23329e43a6b9a1a5b97db04a48
Source dataset
uspto-grants-1982_12
Patent number
US04362740

Reaction notes

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