Cyanamide → HCID 178419031, compound

HRID 1724630

Reaction equation

HRID 1724630 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]#[C:17][NH2:18]>Cl.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][C:17]([NH2:18])=[NH:16])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9864CyanamideHCID 928923-Benzyloxyaniline

Product 1

HCID 178419031HCID 178419031, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

3-benzyloxy aniline (1 g, 5 mmol) and cyanamide (420 mg, 10 mmol) were dissolved in 4 mL of 4N HCl in dioxane and heated to 120° C. overnight. The reaction mixture was cooled to room temperature, quenched with water, and extracted with diethyl ether. The aqueous layer was made basic with 2N NaOH and extracted thrice with dichloromethane. The organic extracts were combined and washed with brine, dried over MgSO4, and concentrated to afford 4 (450 mg) as a light brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water
  3. extractionextracted with diethyl ether
  4. extractionextracted thrice with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62d63ae235024c47abb0b5e832a8f814
Source dataset
uspto-grants-2009_02
Patent number
US07488727B2

Linked notes

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