Hydrochloric Acid → N-Cyano-4-methylbenzamide

HRID 1824013Notes

Reaction equation

HRID 1824013 reaction equation
[N:1]#[C:2][NH2:3].[CH3:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1.Cl>[OH-].[Na+].CCOCC>[CH3:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:1][C:2]#[N:3])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 22149266N-Cyano-4-methylbenzamideYield 84,908.398%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of cyanamide (1.05 g, 0.025 mmol) in 25 ml of sodium hydroxide (10%) was added slowly to a solution of 4-methylbenzoyl chloride (3.3 ml, 0.025 mmol) in ether (8 ml). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture then was cooled in ice bath and acidified with hydrochloric acid (10%) to pH 2. The white solid separated was filtered, washed with water, later hexanes and dried under high vacuum to give the N-(4-methylbenzoyl)cyanamide (3.4 g); m.p. 140–142° C. (lit m.p. 149–150° C.); purity 88% HPLC; 1H-NMR (CD3OD) δ 2.42 (s, 3H, CH3), 7.38 (d, 2H, ArH), 7.78 (d, 2H, ArH).

Workup

  1. temperatureThe reaction mixture then was cooled in ice bath
  2. customThe white solid separated
  3. filtrationwas filtered
  4. washwashed with water, later hexanes
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d2b1d6895f9d45f0b98b1975fd04d731
Source dataset
uspto-grants-2006_05
Patent number
US07041702B1

Reaction notes

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