1-(2,6-Dibromophenyl)thiourea → 2,6-Dibromophenyl isothiocyanate

HRID 1863499Notes

Reaction equation

HRID 1863499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[NH:9][C:10](N)=[S:11]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[N:9]=[C:10]=[S:11]

Participants

3

Reactant 1

HCID 124068471-(2,6-Dibromophenyl)thiourea

Product 1

HCID 126355872,6-Dibromophenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A suspension of 101 g. (0.326 mole) of 1-(2,6-dibromophenyl)thiourea in 1 l. of chlorobenzene was stirred and refluxed 20 hours, and the resulting solution was filtered and evaporated. The tan solid obtained was triturated with boiling petroleum ether and filtered. On cooling, the filtrate deposited 63.4 g. of yellow needles of 2,6-dibromophenylisothiocyanate, m.p. 63°-65°. A portion was recrystallized from ether-petroleum ether to give the analytical sample, m.p. 65°-66°.

Workup

  1. additionA suspension of 101 g
  2. temperaturerefluxed 20 hours
  3. filtrationthe resulting solution was filtered
  4. customevaporated
  5. customThe tan solid obtained
  6. customwas triturated with boiling petroleum ether
  7. filtrationfiltered
  8. temperatureOn cooling
  9. customA portion was recrystallized from ether-petroleum ether
  10. customto give the analytical sample, m.p. 65°-66°

Sources & evidence

ORD record
ord-530c098fedc840bfbd3ae1eee7aef15e
Source dataset
uspto-grants-1979_09
Patent number
US04169154

Reaction notes

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