3-chloro-3-phenyl-1-(3H)-isobenzofuranone → 3-Phenyl-3-[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]-2-benzofuran-1(3H)-one

HRID 615661Notes

Reaction equation

HRID 615661 reaction equation
CC(C)([O-])C.[K+].[C:7]1([N:13]2[C:17]([SH:18])=[N:16][N:15]=[N:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:22](=[O:23])[O:21]1>CN(C)C=O>[C:30]1([C:20]2([S:18][C:17]3[N:13]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:14]=[N:15][N:16]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22](=[O:23])[O:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 35605513-chloro-3-phenyl-1-(3H)-isobenzofuranoneHCID 23665647Potassium tert-butoxideHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 204268383-Phenyl-3-[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 300 ml of dried dimethylformamide, was added 14.56 g (0.12 mol.) of potassium tert-butoxide and 18 g (0.1 mol.) of 1-phenyl-5-mercaptotetrazole. The mixture was stirred for 20 minutes at room temperature. Thereafter, to the mixture cooled to 5° C. and kept there, was gradually added dropwise a solution prepared by adding 25 g (0.1 mol.) of 3-chloro-3-phenylphthalide to 75 ml of dried dimethylformamide. At the conclusion of the dropwise addition, the cooling bath was removed, and the mixture was stirred for 2 hours at room temperature. Thereto, 300 ml of a saturated aqueous solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate repeatedly. The extract was washed with water, and the resulting organic layer was dried over anhydrous sodium sulfate. Sodium sulfate was filtered off with suction, and the filtrate was concentrated to yield 35 g of oily substance. This oily substance was separated and purified by flash column chromatography (silica gel: 700 g, eluate: hexane-ethyl acetate (3:1 by vol.) mixture). Thus, the intended compound, 3-phenyl-3-(1-phenyltetrazole-5-ylthio)phthalide (1), was obtained in the form of white crystals. Yield 21.5 g, Melting Point 137°-139° C.

Workup

  1. temperatureThereafter, to the mixture cooled to 5° C.
  2. additionwas gradually added dropwise a solution
  3. customprepared
  4. additionAt the conclusion of the dropwise addition
  5. customthe cooling bath was removed
  6. stirringthe mixture was stirred for 2 hours at room temperature
  7. additionThereto, 300 ml of a saturated aqueous solution of ammonium chloride was added
  8. extractionThe reaction mixture was extracted with ethyl acetate repeatedly
  9. washThe extract was washed with water
  10. dry with materialthe resulting organic layer was dried over anhydrous sodium sulfate
  11. filtrationSodium sulfate was filtered off with suction
  12. concentrationthe filtrate was concentrated
  13. customto yield 35 g of oily substance
  14. customThis oily substance was separated
  15. custompurified by flash column chromatography (silica gel: 700 g, eluate: hexane-ethyl acetate (3:1 by vol.) mixture)

Sources & evidence

ORD record
ord-73536bcdef8d4d5297b6ca821c4341cc
Source dataset
uspto-grants-1985_02
Patent number
US04500636

Reaction notes

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