Isobutylamine → HCID 178449184, compound

HRID 1788634Notes

Reaction equation

HRID 1788634 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)SC)#[N:2].[CH2:18]([NH2:22])[CH:19]([CH3:21])[CH3:20]>C(#N)C>[C:1]([N:3]=[C:4]([NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[NH:22][CH2:18][CH:19]([CH3:21])[CH3:20])#[N:2]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 10198757HCID 10198757, compound

Product 1

HCID 178449184HCID 178449184, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 12.3 g of N-cyano-N'-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 20 ml of isobutylamine in 100 ml of acetonitrile was heated at reflux with stirring for 100 hours. The solvent was then removed by evaporation in vacuo. The residual oil was dissolved in methylene chloride and the solution was washed with three 80 ml portions of 3N hydrochloric acid and then dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the methylene chloride was removed from the filtrate by evaporation in vacuo, leaving N"-cyano-N-isobutyl-N'-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as 11.6 g of a pale yellow, viscous oil.

Workup

  1. temperatureat reflux
  2. customThe solvent was then removed by evaporation in vacuo
  3. dissolutionThe residual oil was dissolved in methylene chloride
  4. washthe solution was washed with three 80 ml portions of 3N hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe sodium sulfate was removed by filtration
  7. customthe methylene chloride was removed from the filtrate by evaporation in vacuo

Sources & evidence

ORD record
ord-db01fe2c132d47d2a201a259adc7b8ec
Source dataset
uspto-grants-1987_08
Patent number
US04684398

Reaction notes

Loading…