Diphosgene → HCID 54017826, compound

HRID 864316Notes

Reaction equation

HRID 864316 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.Cl[C:18](OC(Cl)(Cl)Cl)=[O:19]>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1)=[C:18]=[O:19]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 53722619HCID 53722619, compound

Product 1

HCID 54017826HCID 54017826, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

tert-Butyl (3-isocyanatophenylthio)acetate can be obtained in the following manner: a solution of 2.9 g of tert-butyl (3-aminophenylthio)acetate in 25 cm3 of toluene is added dropwise, at a temperature near to -30° C., to a suspension of 0.24 g of carbon in 1.46 cm3 of trichloromethyl chloroformate and 15 cm3 of toluene. The reaction mixture is stirred for 2 hours at a temperature near to 20° C. and then for 2 hours and 30 minutes at a temperature near to 110° C. The reaction mixture is then cooled to a temperature near to 20° C., degassed by bubbling nitrogen in, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 50° C. 2.6 g of tert-butyl (3-isocyanatophenylthio)acetate are thus obtained in the form of an oil which is used as such in the subsequent syntheses.

Workup

  1. waitfor 2 hours
  2. custom30 minutes
  3. customnear to 110° C
  4. temperatureThe reaction mixture is then cooled to a temperature near to 20° C.
  5. customdegassed
  6. customby bubbling nitrogen in
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 50° C

Sources & evidence

ORD record
ord-89d6ea73aae34dfb9b409200ac8c653b
Source dataset
uspto-grants-1996_10
Patent number
US05563136

Reaction notes

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