1-Bromooctane → HCID 178443887, compound

HRID 267181Notes

Reaction equation

HRID 267181 reaction equation
[NH2:1][C:2]([NH:4][C:5]([NH2:7])=[S:6])=[S:3].[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>COCCO>[CH2:8]([SH:3]=[C:2]([NH:4][C:5]([NH2:7])=[S:6])[NH2:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 81401-BromooctaneHCID 2758725Dithiobiuret

Product 1

HCID 178443887HCID 178443887, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
0 °C

Procedure

The S-octyldithiobiuret was prepared as follows: To 135 g of dithiobiuret in 300 ml ethyleneglycol monomethyl ether were added 210 g of n-octyl bromide dropwise at 70°C. After 12 hours the solvent was distilled off at 12 mm. The residue was dissolved in toluene and hexane was added after which the mixture was cooled at 0°C. The solvent was decanted from the semicrystalline precipitate which was dissolved again in glacial acetic acid. The solution was poured on icewater and stirred for 2 hours. The solid was filtered, stirred with hexane in a beaker until it had completely crystallized, filtered and dried. The product had a melting point of 75°-77°C.

Workup

  1. distillationAfter 12 hours the solvent was distilled off at 12 mm
  2. dissolutionThe residue was dissolved in toluene
  3. additionhexane was added after which the mixture
  4. customThe solvent was decanted from the semicrystalline precipitate which
  5. dissolutionwas dissolved again in glacial acetic acid
  6. additionThe solution was poured on icewater
  7. filtrationThe solid was filtered
  8. stirringstirred with hexane in a beaker until it
  9. customhad completely crystallized
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-53003dedb71c442da43dea05e7b5de0e
Source dataset
uspto-grants-1976_03
Patent number
US03941745

Reaction notes

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