HCID 20426825, compound → HCID 20426832, compound

HRID 615664Notes

Reaction equation

HRID 615664 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][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])[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:7]1([N:13]2[C:17]([S:18][C:20]3([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:22](=[O:23])[O:21]3)=[N:16][N:15]=[N:14]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 20426825HCID 20426825, compoundHCID 23665647Potassium tert-butoxideHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 20426832HCID 20426832, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 300 ml of dried dimethylformamide, was added 5.6 g (0.05 mol.) of potassium tert-butoxide and 8.9 g (0.05 mol.) of 1-phenyl-5-mercaptotetrazole. The mixture was stirred for 20 minutes at room temperature. Thereafter, to the mixture which was cooled to 5° C. and kept there, was added gradually dropwise a solution prepared by adding 13 g (0.04 mol.) of 3-chloro-3-(2,4-dichlorophenyl)phthalide in 75 ml of dried dimethylformamide. After dropwise addition, the cooling bath was removed, and the mixture was stirred for 5 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 23.5 g of oily substance. This oily substance was separated and purified by flash column chromatography (silica gel: 800 g, eluate: hexane-ethyl acetate (3:1 by volume) mixture). Thus, the intended compound, 3-(1-phenyl-tetrazole-5-ylthio)-3-(2,4-dichlorophenyl)phthalide (3), was obtained in a form of white crystals. Yield 7.8 g, Melting Point 148° to 149° C.

Workup

  1. temperatureThereafter, to the mixture which was cooled to 5° C.
  2. additionwas added gradually dropwise a solution
  3. customprepared
  4. additionAfter dropwise addition
  5. customthe cooling bath was removed
  6. stirringthe mixture was stirred for 5 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 23.5 g of oily substance
  14. customThis oily substance was separated
  15. custompurified by flash column chromatography (silica gel: 800 g, eluate: hexane-ethyl acetate (3:1 by volume) mixture)

Sources & evidence

ORD record
ord-727015ac7c3449c5a1a5dce68db7ce58
Source dataset
uspto-grants-1985_02
Patent number
US04500636

Reaction notes

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