Hydrochloric Acid → HCID 178437930, compound

HRID 1416415Notes

Reaction equation

HRID 1416415 reaction equation
[CH2:1]([C:3]1[S:7][C:6](=[NH:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])=[CH:12][CH:11]=2)[N:4]=1)[CH3:2].C[Sn]([N:28]=[N+:29]=[N-:30])(C)C.Cl>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[S:7][C:6](=[NH:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:30][N:29]=[N:28][N:23]=3)=[CH:12][CH:11]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5104973Azido(trimethyl)stannaneHCID 15859426HCID 15859426, compound

Product 1

HCID 178437930HCID 178437930, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 10 ml of toluene, 1.6 g of 5-ethyl-2-imino-3-(2'-cyanobiphenyl-4-yl)methyl-1,3,4-thiadiazoline and 1.1 g of trimethyltin azide were suspended, followed by heating under reflux for 4 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 fractions thus obtained were distilled off under reduced pressure. To the resulting 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 successively washed with water, ethanol and diethyl ether and then dried, whereby 290 mg of the title compound was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. washeluted
  5. customThe eluate fractions thus obtained
  6. distillationwere distilled off under reduced pressure
  7. additionTo the resulting 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 successively washed with water, ethanol and diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-3790048264c7498db8764ba105aae1c4
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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