Potassium Hydroxide → N-(2-morpholinophenyl)cyanamide

HRID 1588683Notes

Reaction equation

HRID 1588683 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([NH2:16])=S)[CH2:3][CH2:2]1.[OH-].[K+].O.O.O.C([O-])(=O)C.[Pb+2].C([O-])(=O)C>O>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]#[N:16])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 22456Lead diacetate trihydrateHCID 27411931-(2-Morpholinophenyl)thiourea

Product 1

HCID 15746517N-(2-morpholinophenyl)cyanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

1-(2-morpholinophenyl)thiourea (10.5 g) was suspended in boiling water (80 ml) and a solution of potassium hydroxide (25.2 g) in hot water (70 ml) was added. The mixture was heated to 90°0 C. and aliquot portions of a hot solution of lead acetate trihydrate (17.5 g) in water (80 ml) added and the mixture heated under reflux for 10 minutes and cooled to ambient temperature. The mixture was filtered and the filtrate acidified with acetic acid to pH 6. The solid which formed was separated by filtration, washed with water and recrystallised from ethylacetate to give N-(2-morpholinophenyl)cyanamide (m.p. 175°-176° C.).

Workup

  1. temperatureThe mixture was heated to 90°0 C
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 10 minutes
  4. filtrationThe mixture was filtered
  5. customThe solid which formed
  6. customwas separated by filtration
  7. washwashed with water
  8. customrecrystallised from ethylacetate

Sources & evidence

ORD record
ord-f74e98d3c42e4452ac65ed4a9be53fe7
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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