Hydrogen Bromide → HCID 22118520, compound

HRID 365288Notes

Reaction equation

HRID 365288 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH:5]=[CH:4][N:3]=[CH:2]1.[BrH:12].C(O[CH2:16][CH3:17])C.[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>CO>[BrH:12].[BrH:12].[Br:12][C:17]1[CH:16]=[CH:22][C:18]([CH2:5][N:1]([CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[S:11])[C:2]2[CH:20]=[CH:19][CH:18]=[CH:22][N:3]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 11084267HCID 11084267, compound

Product 1

HCID 22118520HCID 22118520, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-1-(4-bromobenzyl)-1-(pyrid-2-yl)propane-1,3-diamine (616 mg, 1.92 mmol) in THF (15 mL) was treated dropwise with 3-(imidazol-1-yl)propyl isothiocyanate (323 mg, 1.92 mmol) in THF (10 mL) under a nitrogen atmosphere. After stirring overnight at room temperature, the solid was filtered. Evaporation of the filtrate under reduced pressure gave a yellow oil which was dissolved in methanol and acidified with methanolic hydrogen bromide. Addition of diethyl ether afforded a cloudy solution which produced a light tan solid upon standing in the refrigerator. The solid was filtered and dried to yield 0.94 g (75%) of the title compound. Recrystallization from absolute ethanol-diethyl ether afforded an analytical sample.

Workup

  1. filtrationthe solid was filtered
  2. customEvaporation of the filtrate under reduced pressure
  3. customgave a yellow oil which
  4. customafforded a cloudy solution which
  5. customproduced a light tan solid
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-e719fd3867cb4957856748e9d27f59ea
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

Loading…