4-Chlorophenyl isothiocyanate → HCID 54471914, compound

HRID 2072446Notes

Reaction equation

HRID 2072446 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][CH:10]2[CH:5]3[CH2:6][CH:7]4[CH:9]2[CH:8]4[CH:4]13.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[S:21])=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[S:21])[NH:2][CH:3]2[CH2:11][CH:10]3[CH:5]4[CH2:6][CH:7]5[CH:9]3[CH:8]5[CH:4]24)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 86735104HCID 86735104, compound

Product 1

HCID 54471914HCID 54471914, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

8-Aminotetracyclo[4,3,0,02,4,03,7 ]nonane hydrochloride (0.5 g.) (prepared as described in U.K. Patent Specification No. 1,180,749) was dissolved in a mixture of chloroform (25 ml.) and triethylamine (0.33 g.). To this solution was added p-chlorophenylisothiocyanate (0.5 g.) and the mixture refluxed for 16 hours. The chloroform solution, after cooling, was washed successively with 10 ml. portions of 2N HCl, water and saturated brine, and then dried over anhydrous MgSO4. After filtration, the solvent was evaporated in vacuo and the residue crystallised from toluene/cyclohexane (1:2 v/v) to give 8-[3-(p-chlorophenyl)thioureido]tetracyclo[4,3,0,02,4,03,7 ]-nonane, m.p. 168°-170°.

Workup

  1. temperaturethe mixture refluxed for 16 hours
  2. washwas washed successively with 10 ml
  3. dry with materialportions of 2N HCl, water and saturated brine, and then dried over anhydrous MgSO4
  4. filtrationAfter filtration
  5. customthe solvent was evaporated in vacuo
  6. customthe residue crystallised from toluene/cyclohexane (1:2 v/v)

Sources & evidence

ORD record
ord-f4bbd7018b6f4765aab3fc5da484ab5c
Source dataset
uspto-grants-1977_09
Patent number
US04051256

Reaction notes

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