Water → Ethanimidamide, N,N'-diphenyl-

HRID 1658182Notes

Reaction equation

HRID 1658182 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH:8]1(SCl)[CH2:13][CH2:12][CH2:11][CH2:10]C1.O.C[N:18]([CH3:21])C=O>>[C:21]1([NH:18][C:6](=[N:3][C:4]2[CH:5]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:7])[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 87312Cyclohexanesulfenyl chloride2×

Product 1

HCID 12117Ethanimidamide, N,N'-diphenyl-

Conditions

Temperature
0 °C

Procedure

The N,N'-diphenylacetamidine which is prepared according to the above paragraph is then placed in a flask along with an acid scavenger comprising triethylamine using dimethylformamide as a solvent. The mixture is cooled to a temperature of 0° C. and maintained thereat while an equimolar amount of cyclohexanesulfenyl chloride is slowly added thereto dropwise. The temperature of the reaction will range from about 0° to about 10° C. with continuous stirring. Following the completion of the addition of the cyclohexanesulfenyl chloride, the reaction mixture is stirred for an additional period of 1 hour while allowing the temperature of the solution to reach room temperature. Following this, water is added and the organic layer which separates out is thereafter washed several times with water, dried over magnesium sulfate and subjected to vacuum to remove the dimethylformamide solvent. The resulting material will slowly crystallize and the crystals comprising N,N'-diphenyl-N-cyclohexylthioacetamidine will be recovered by filtration.

Workup

  1. customis then placed in a flask along with an acid scavenger
  2. temperaturemaintained
  3. customThe temperature of the reaction
  4. customwill range from about 0° to about 10° C. with continuous stirring
  5. customto reach room temperature
  6. additionis added
  7. washthe organic layer which separates out is thereafter washed several times with water
  8. dry with materialdried over magnesium sulfate
  9. customto remove the dimethylformamide solvent
  10. customThe resulting material will slowly crystallize
  11. filtrationwill be recovered by filtration

Sources & evidence

ORD record
ord-4a8c2401a88946a3a02625de29b62c0e
Source dataset
uspto-grants-1976_06
Patent number
US03963683

Reaction notes

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