Thiophosgene → HCID 21765455, compound

HRID 2072444Notes

Reaction equation

HRID 2072444 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH:4]3[CH:5]([CH2:6]2)[CH:3]13.[C:9](Cl)(Cl)=[S:10]>C(Cl)(Cl)Cl>[N:1]([CH:2]1[CH:7]2[CH2:8][CH:4]3[CH:5]([CH2:6]2)[CH:3]13)=[C:9]=[S:10]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 53740364HCID 53740364, compound

Product 1

HCID 21765455HCID 21765455, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3-Aminotricyclo[2,2,1,02,6 ]heptane (21 g.) (prepared as described in U.K. Patent Specification No. 1,051,319), was dissolved in chloroform (25 ml.) and added slowly, below 10°, to a stirred solution of thiophosgene (22 g.) in chloroform (20 ml.). When addition was complete the mixture was allowed to attain ambient temperature and stirred a further 2 hours. The chloroform solution was consecutively washed with 20 ml. portions of water, 1N NaOH, and water again, dried over anhydrous MgSO4, filtered and the chloroform evaporated in vacuo. The residual oil was fractionally distilled in vacuo to give 3-isothiocyanatotricyclo[2,2,1,02,6 ]heptane, b.p. 70°-76° at 0.4 mm. Hg. pressure.

Workup

  1. additionWhen addition
  2. customto attain ambient temperature
  3. washThe chloroform solution was consecutively washed with 20 ml
  4. dry with materialportions of water, 1N NaOH, and water again, dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customthe chloroform evaporated in vacuo
  7. distillationThe residual oil was fractionally distilled in vacuo

Sources & evidence

ORD record
ord-12f76c9174cc43ba8cdf2fd36b802b70
Source dataset
uspto-grants-1977_09
Patent number
US04051256

Reaction notes

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