Benzoyl chloride → Benzamide, N-cyano-

HRID 1608111

Reaction equation

HRID 1608111 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:10]#[C:11][NH2:12].[Na]>C(OCC)C>[C:1]([NH:12][C:11]#[N:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 57375518Cyanamidnatrium

Product 1

HCID 84805Benzamide, N-cyano-Yield 89.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Benzoylcyanamide was prepared by the addition of benzoyl chloride (6.33 g, 0.045 mol) in 100 ml of diethyl ether to a suspension of monosodium cyanamide (5.76 g, 0.090 mol) in 100 ml of ether at 4° C. The reaction was stirred overnight at room temperature and the pale yellow solid which formed was collected and dissolved in water. On acidification of the solution to pH 1, a precipitate formed which was collected and recrystallized from ethyl acetate (EtOAc)/petroleum ether (30°-60° C.) to give 2 (5.89 g, 89.7% yield), mp 140°-142° C. [reported mp 139°-140° C⟧ Anal. Calcd for C8H6H2O: C, 65.75; H, 4.11; N, 19.18. Found: C, 65.79; H, 4.35; N, 19.04.

Workup

  1. customthe pale yellow solid which formed
  2. customwas collected
  3. dissolutiondissolved in water
  4. customOn acidification of the solution to pH 1, a precipitate formed which
  5. customwas collected
  6. customrecrystallized from ethyl acetate (EtOAc)/petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-774f5d7c186941edbbddc091bf02967a
Source dataset
uspto-grants-1989_09
Patent number
US04870056

Linked notes

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