Triethylamine → N,N'-Di-p-tolyl-formamidine

HRID 1658184Notes

Reaction equation

HRID 1658184 reaction equation
C(N(CC)CC)C.C(SCl)CCCCCCCCC.[C:20]1([CH3:47])[CH:25]=[CH:24][C:23]([N:26](SCCCCCCCCCC)[CH:27]=[N:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[CH:22][CH:21]=1>C1C=CC=CC=1>[C:32]1([CH3:35])[CH:33]=[CH:34][C:29]([NH:28][CH:27]=[N:26][C:23]2[CH:22]=[CH:21][C:20]([CH3:47])=[CH:25][CH:24]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21528748HCID 21528748, compoundHCID 21983338HCID 21983338, compound2×

Product 1

HCID 159293N,N'-Di-p-tolyl-formamidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

The N,N'-di-p-tolylformamidine which is prepared according to the above paragraph is then placed in a flask which is cooled to a temperature of about 0° C. by means of an ice bath. In addition, there was also present in the flask 100 grams of triethylamine and 200 cc. of benzene. When the mixture has reached the desired reduced temperature, decanesulfenyl chloride is slowly added dropwise accompanied by continuous stirring. Upon completion of the addition of the decanesulfenyl chloride, the mixture is stirred for an additional period of 1 hour and then allowed to warm to room temperature. Upon standing the desired product comprising N,N'-di-p-tolyl-N-decylthioformamidine crystallizes, is filtered, washed and recovered.

Workup

  1. customis then placed in a flask
  2. additionis slowly added dropwise
  3. temperatureto warm to room temperature
  4. customcrystallizes
  5. filtrationis filtered
  6. washwashed
  7. customrecovered

Sources & evidence

ORD record
ord-b8a64a00de7841a389ab3d3387f22849
Source dataset
uspto-grants-1976_06
Patent number
US03963683

Reaction notes

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