Aniline → N-benzene sulfonyl phenyl cyanamide

HRID 616564Notes

Reaction equation

HRID 616564 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2C[CH2:15][N:10](CC2)C1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N#CCl>C1COCC1>[C:16]1([S:22]([N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:15]#[N:10])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 7369Benzenesulfonyl chlorideHCID 9237DabcoHCID 10477Cyanogen Chloride

Product 1

HCID 21323003N-benzene sulfonyl phenyl cyanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a 3 liter 3-necked flask equipped with a stirrer, addition funnel, thermometer, and drying tube was charged 93.1g (1.0 mole) of aniline, 111g (1.1 moles) of triethylene diamine and 250 ml. of tetrahydrofuran. To this reaction mixture was added dropwise a solution of 176.6g (1 mole) of benzenesulfonyl chloride in 300 ml. of tetrahydrofuran. The reaction mixture was stirred at room temperature for 2.5 hours and was then filtered. To the filtrate was added 111g of triethylene diamine and this solution was added dropwise to a solution of 87g (1.41 moles) of cyanogen chloride in 100 ml. of THF which was maintained at -5° C. with cooling. After this addition was complete the stirred reaction mixture was allowed to return to room temperature over a 16 1/2 hour period. The reaction mixture was filtered and the filament was added to water to precipitate the product. The product was recrystallized from aqueous methanol to yield 218g (84.7%) of N-benzene sulfonyl phenyl cyanamide, m.p. 65°-66° C.

Workup

  1. customTo a 3 liter 3-necked flask equipped with a stirrer, addition funnel
  2. customthermometer, and drying tube
  3. filtrationwas then filtered
  4. additionTo the filtrate was added 111g of triethylene diamine
  5. temperaturewith cooling
  6. additionAfter this addition
  7. customthe stirred reaction mixture
  8. customto return to room temperature over a 16 1/2 hour period
  9. filtrationThe reaction mixture was filtered
  10. additionthe filament was added to water
  11. customto precipitate the product
  12. customThe product was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-9de476f1dce84fc7bd71162ca73c4ade
Source dataset
uspto-grants-1978_02
Patent number
US04075185

Reaction notes

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