4-Nitrobenzyl chloride → HCID 178526642, compound

HRID 1710016Notes

Reaction equation

HRID 1710016 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[S:8][S:7][C:6](=[S:9])[N:5]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1)([O-:12])=[O:11]>O.C(O)C.C(Cl)Cl>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][S:8][C:4]2[N:5]=[C:6]([SH:9])[S:7][N:3]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

7

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 14798Sodium HydroxideHCID 2735329Xanthane hydride

Product 1

HCID 178526642HCID 178526642, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.2 grams (0.055 mole) of sodium hydroxide in 7 ml of water and 20 ml of ethanol was stirred and 4.0 grams (0.027 mole) of 5-amino-1,2,4-dithiazol-3-thione was added portionwise. After all of the 5-amino intermediate was in solution, 4.7 grams (0.027 mole) of 4-nitrophenylmethyl chloride was added dropwise. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in 20 ml of water then extracted with two 25 ml portions of diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid to yield a gummy solid. The solid was extracted from the aqueous layer with two 25 ml portions of ethyl acetate. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a gummy solid. The solid was dissolved in methylene chloride and filtered to remove a small amount of insoluble material. The filtrate was concentrated under reduced pressure to yield 2.8 grams of 3-(4-nitrophenylmethylthio)-5-mercapto-1,2,4-thiadiazole as a solid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise
  2. additionUpon completion of addition the reaction mixture
  3. concentrationThe reaction mixture was concentrated under reduced pressure to a residue
  4. dissolutionThe residue was dissolved in 20 ml of water
  5. extractionthen extracted with two 25 ml portions of diethyl ether
  6. customto yield a gummy solid
  7. extractionThe solid was extracted from the aqueous layer with two 25 ml portions of ethyl acetate
  8. dry with materialThe combined extracts were dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customto yield a gummy solid
  12. filtrationfiltered
  13. customto remove a small amount of insoluble material
  14. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0957fb0343f4dfc8866ce6d26718db6
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

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