Hydrochloric Acid → HCID 178437930, compound

HRID 1416414Notes

Reaction equation

HRID 1416414 reaction equation
Br.[CH2:2]([C:4]1[S:8][C:7](=[NH:9])[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:5]=1)[CH3:3].C[Sn]([N:29]=[N+:30]=[N-:31])(C)C.Cl>C1(C)C=CC=CC=1>[CH2:2]([C:4]1[S:8][C:7](=[NH:9])[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:31][N:30]=[N:29][N:24]=3)=[CH:13][CH:12]=2)[N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5104973Azido(trimethyl)stannaneHCID 67582513HCID 67582513, compound

Product 1

HCID 178437930HCID 178437930, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml of toluene, 2.0 g of 5-ethyl-2-imino-3-(2'-cyanobiphenyl-4-yl)methyl-1,3,4-thiadiazoline.hydrobromide and 1.1 g of trimethyltin azide were suspended, followed by heating under reflux for 6 hours. After cooling, the reaction mixture was subjected to column chromatography on a silica gel and eluted using chloroform:methanol (20:1)→chloroform:methanol:acetic acid (20:10:1). The eluate fraction thus obtained were then distilled off under reduced pressure. To the residue, 40 ml of 2N sodium hydroxide and 40 ml of ethyl acetate were added. The aqueous layer so obtained was neutralized with 12N hydrochloric acid and powders so precipitated were collected by filtration. The powders were washed successively with water, ethanol and then diethyl ether and then dried, whereby 56 mg of the title compound was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. washeluted
  5. customThe eluate fraction thus obtained
  6. distillationwere then distilled off under reduced pressure
  7. additionTo the residue, 40 ml of 2N sodium hydroxide and 40 ml of ethyl acetate were added
  8. customThe aqueous layer so obtained
  9. customso precipitated
  10. filtrationwere collected by filtration
  11. washThe powders were washed successively with water, ethanol
  12. dry with materialdiethyl ether and then dried

Sources & evidence

ORD record
ord-5f73d11199b742d58fc3cadf6925d528
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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