Carbon Tetrachloride → HCID 19910784, compound

HRID 1534103Notes

Reaction equation

HRID 1534103 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=S)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[N:12][C:13]([CH2:16][CH3:17])([CH2:18][CH3:19])[CH2:14][CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020149HCID 15020149, compound

Product 1

HCID 19910784HCID 19910784, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 810 mg of N-(3,5-dichlorophenyl)-N'-(1,1-diethylpropyl)thiourea produced in Example A-7 and 800 mg of triphenylphosphine in 10 ml of dichloromethane were added 380 mg of triethylamine and 590 mg of carbon tetrachloride. The mixture was refluxed for 4 hours and evaporated in vacuo. The residue was stirred with n-hexane and filtered to remove solid matter. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography using n-hexane as a solvent to give 640 mg of N-(3,5-dichlorophenyl)-N'-(1,1-diethylpropyl)carbodiimide as an oil. To a solution of this oil in 5 ml of DMF were added 470 mg of cyanamide and 0.05 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 3 hours, cooled to room temperature and poured into water. The resulting crystals were collected and recrystallized from benzene to give 480 mg of the title compound as colorless needles melting at 178.5°-180.5° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customevaporated in vacuo
  3. filtrationfiltered
  4. customto remove solid matter
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7982934c01f84cb296c51444100875a7
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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