Sodium Cyanate → HCID 12803105, compound

HRID 1904769Notes

Reaction equation

HRID 1904769 reaction equation
[O-:1][C:2]#[N:3].[Na+].[NH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]#[N:17]>O.C(O)(=O)C>[C:16]([CH2:15][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([NH:5][C:2]([NH2:3])=[O:1])[CH:7]=2)[NH:11][CH:10]=1)#[N:17]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 12803100HCID 12803100, compound

Product 1

HCID 12803105HCID 12803105, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium cyanate (1.2 g) in water (10 ml) was added to a stirred solution of 5-amino-1H-indole-3-aceto-nitrile (1.5 g) in glacial acetic acid (5 ml) and water (10 ml). Stirring was continued until a brown gum precipitated (10 min). The aqueous layer was then decanted off, and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with sodium carbonate soln. (2N, 2×100 ml), dried (Na2SO4) and evaporated in vacuo to yield the crude urea as an off-white solid (0,3 g). The brown gum was purified by column chromatography (Kieselgel 60, 25 g) using ethyl acetate as eluant to yield more of the crude urea (0.1 g). The crude urea was then crystallised from isopropanol to yield the title compound as a fawn solid (0.3 g) m.p. 200°-204°.

Workup

  1. customprecipitated (10 min)
  2. customThe aqueous layer was then decanted off
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washThe combined extracts were washed with sodium carbonate soln
  5. dry with material(2N, 2×100 ml), dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto yield the crude urea as an off-white solid (0,3 g)
  8. customThe brown gum was purified by column chromatography (Kieselgel 60, 25 g)
  9. customto yield more of the crude urea (0.1 g)
  10. customThe crude urea was then crystallised from isopropanol

Sources & evidence

ORD record
ord-d7e49b7ea3034a5a981eb7bb28d73db0
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

Loading…