Carbon Tetrachloride → N-(Cyclohexylcarbonimidoyl)benzenamine

HRID 1649858Notes

Reaction equation

HRID 1649858 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=S)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[CH:11]1([N:10]=[C:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 766306N-Cyclohexyl-N'-phenylcarbamimidothioic acid

Product 1

HCID 10921546N-(Cyclohexylcarbonimidoyl)benzenamineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 2.0 g (8.55 mmol) of N-cyclohexyl-N'-phenylthiourea, 2.9 g (11.1 mmol) of triphenyl phosphine and 1.16 cm3 (12 mmol) of carbon tetrachloride in 12 cm3 of methylene chloride, is treated with 1.19 cm3 (8.55 mmol) of triethylamine. The solution is heated for 2 hours, the precipitate which forms is eliminated by filtration and the filtrate is concentrated to dryness. The residue obtained is extracted with hexane and then filtered. The filtrates are then concentrated to dryness and 1.7 g (yield 100%) of the desired carbodiimide is obtained in the form of an oil.

Workup

  1. temperatureThe solution is heated for 2 hours
  2. filtrationthe precipitate which forms is eliminated by filtration
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe residue obtained
  5. extractionis extracted with hexane
  6. filtrationfiltered
  7. concentrationThe filtrates are then concentrated to dryness

Sources & evidence

ORD record
ord-01f18543136443c6b231024d36324b2a
Source dataset
uspto-grants-1990_05
Patent number
US04921939

Reaction notes

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