Sodium dicyanamide → HCID 178512346, compound

HRID 543243Notes

Reaction equation

HRID 543243 reaction equation
Cl.[CH:2]1([NH2:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[N-:13]([C:16]#[N:17])[C:14]#[N:15].[Na+]>O>[C:14]([NH:13][C:16](=[NH:17])[NH:12][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1)#[N:15]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 101926091-Naphthylamine, 1,2,3,4-tetrahydro-, hydrochloride

Product 1

HCID 178512346HCID 178512346, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 18.4 grams (g) of 1,2,3,4-tetrahydro-1-naphthylamine hydrochloride and 8.90 g of sodium dicyanamide in 220 milliliters (ml) of water was heated at 95° C. (steam bath) for 21 hours, after which time a viscous oil had precipitated from the hot solution. The reaction mixture was then cooled and extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and the sodium sulfate removed by filtration. The methylene chloride was then removed by evaporation in vacuo, leaving the crude product as a pale yellow gum. The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid, melting point (mp) 153.5°-156.5° C. Recrystallization from aqueous ethanol gave 3.87 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as a white, crystalline solid, mp 157°-158° C.

Workup

  1. customafter which time a viscous oil had precipitated from the hot solution
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customthe sodium sulfate removed by filtration
  7. customThe methylene chloride was then removed by evaporation in vacuo
  8. customleaving the crude product as a pale yellow gum
  9. customThe gum was crystallized from isopropyl acetate
  10. customto give an off-white, crystalline solid
  11. custompoint (mp) 153.5°-156.5° C
  12. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-63a99f02a1f6486a8beae3ed66d07af4
Source dataset
uspto-grants-1987_04
Patent number
US04661520

Reaction notes

Loading…