p-Toluenesulfonyl isocyanate → HCID 9837522, compound

HRID 876105Notes

Reaction equation

HRID 876105 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]1([CH3:17])[CH:10]=[CH:9][C:8]([S:11](N=C=O)(=[O:13])=[O:12])=[CH:7][CH:6]=1>O1CCOCC1>[C:5]1([CH3:17])[CH:10]=[CH:9][C:8]([S:11]([NH:1][C:2]([NH2:4])=[S:3])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 2723790Thiourea

Product 1

HCID 9837522HCID 9837522, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 mL RBF equipped with a condenser, thermo-probe, sealed system nitrogen purge, pressure-equilibrated addition funnel and magnetic stirrer were placed thiourea (9.36 g, 0.12 mol) and dioxane (50 mL). The mixture was warmed to a temperature of 100° C. to encourage dissolution. The mixture was then cooled to a temperature of about 20° C., at which point para-toluenesulfonylisocyanate (25.0 g, 0.12 mol) was added slowly over a period of time of 1 hour. A milky-white suspension was observed to form. The temperature was maintained with an ice-water bath between 20° C. and 32° C. The reaction mixture was stirred overnight at room temperature before it was concentrated in vacuo at a temperature of 40° C. to yield a white solid that was further dried to constant weight in vacuo at a temperature of 50° C. and a pressure of <1 mTorr.

Workup

  1. customIn a 100 mL RBF equipped with a condenser
  2. customthermo-probe, sealed system nitrogen
  3. custompurge
  4. custompressure-equilibrated addition funnel and magnetic stirrer were placed
  5. dissolutiondissolution
  6. additionwas added slowly over a period of time of 1 hour
  7. customto form
  8. temperatureThe temperature was maintained with an ice-water bath between 20° C. and 32° C
  9. concentrationwas concentrated in vacuo at a temperature of 40° C.
  10. customto yield a white solid
  11. customthat was further dried to constant weight in vacuo at a temperature of 50° C.

Sources & evidence

ORD record
ord-511a88197b3e40cba28f85b9c63bea5f
Source dataset
uspto-grants-2015_03
Patent number
US08986847B2

Reaction notes

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