Hydrochloric Acid → HCID 178419031, compound

HRID 6853

Reaction equation

HRID 6853 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-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (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 under vacuum overnight to afford 23.8 g in 98.4% yield. 1H NMR (MeOH-d4) δ 6.4–7.5 (m, 9H), 5.1 (s, 2H).

Workup

  1. temperaturethen cooled to ambient temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe solid product was dried under vacuum overnight
  4. customto afford 23.8 g in 98.4% yield

Sources & evidence

ORD record
ord-e6b1f13036c244b682cb1d3247b19d66
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Linked notes

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