Hydrochloric Acid → HCID 178419031, compound

HRID 2120089Notes

Reaction equation

HRID 2120089 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]#[C:17][NH2:18].Cl.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:17]([NH2:18])=[NH:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 14798Sodium HydroxideHCID 928923-Benzyloxyaniline

Product 1

HCID 178419031HCID 178419031, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 3-benzyloxy-phenylamine (20.0 g, 100.35 mmol) in 150 ml 1,4-dioxane in a 500 ml round bottom flask was added cyanamide (7.39 g, 175.95 mmol) followed by HCl in 1,4-dioxane (4M, 44 ml, 176.00 mmol). The resulting suspension was stirred and heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature then NaOH (6N, 35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml, in vacuo, and the resulting precipitate was collected by filtration. The solid product was dried in vacuo overnight to afford the aryl guanidine 9 (23.8 g) in 98.4% yield. 1H NMR (MeOH-d4) δ 6.4-7.5 (m, 9H), 5.1 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe solid product was dried in vacuo overnight

Sources & evidence

ORD record
ord-988d65f024774c949eda26611db224ff
Source dataset
uspto-grants-2004_02
Patent number
US06689778B2

Reaction notes

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