Cyanamide → HCID 178448970, compound

HRID 377091Notes

Reaction equation

HRID 377091 reaction equation
[N:1]#[C:2][NH2:3].Cl.C([NH:9][C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[O:11])(C)(C)C>O>[C:14]([N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:2]([NH2:3])=[NH:1])=[CH:18][CH:19]=1)[C:10]([NH2:9])=[O:11])([CH3:19])([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 9864Cyanamide2×HCID 22010090HCID 22010090, compound

Product 1

HCID 178448970HCID 178448970, compoundYield 142.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
62.5 °C

Procedure

Cyanamide (100 g, 2.4 mol) was placed in a 500 mL round bottom flask and heated to 60-65° C. until the material completely melted. N-tert-butyl-N'-4-aminobenzylurea hydrochloride, (25.3 g, 97.8 mmol) was then added directly to the liquid cyanamide and the resulting yellow solution was stirred at 60-65° C. an additional two hours. Water (100 mL) was subsequently added to the solution followed by cooling to room temperature. The aqueous solution was washed with ethyl ether (1 L) followed by back extraction of the organic phase with water (2×100 mL). The combined aqueous layers were again washed with ethyl ether (500 mL) and the aqueous solution cooled in an ice water bath followed by basification with aqueous sodium hydroxide (10M, 100 mL). The resulting insoluble oil slowly crystalized and was collected by filtration. The material then was washed with water and dried in vacuo to give N-tert-butyl-N-4-guanidinobenzylurea (18.3 g, 70.8%) as a colorless crystalline solid.

Workup

  1. temperatureby cooling to room temperature
  2. washThe aqueous solution was washed with ethyl ether (1 L)
  3. extractionfollowed by back extraction of the organic phase with water (2×100 mL)
  4. washThe combined aqueous layers were again washed with ethyl ether (500 mL)
  5. temperaturethe aqueous solution cooled in an ice water bath
  6. customThe resulting insoluble oil slowly crystalized
  7. filtrationwas collected by filtration
  8. washThe material then was washed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a121e17d7102430f9e953b8273885c20
Source dataset
uspto-grants-2000_02
Patent number
US06022969

Reaction notes

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