Carbon Tetrachloride → HCID 19910777, compound

HRID 1534100Notes

Reaction equation

HRID 1534100 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH3:18])([CH3:17])[CH:14]([CH3:16])[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(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[N:12][C:13]([CH3:17])([CH3:18])[CH:14]([CH3:15])[CH3:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020147HCID 15020147, compound

Product 1

HCID 19910777HCID 19910777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.3 g of N-(3,5-dichlorophenyl)-N'-(1,1,2-trimethylpropyl)thiourea produced in Example A-4 in 50 ml of dichloromethane were added 3.9 g of triphenylphosphine, 2.4 g of carbon tetrachloride and 1.5 g of triethylamine. The mixture was refluxed for 3 hours and evaporated in vacuo. The residue was extracted with petroleum ether. The extract was evaporated in vacuo to give N-(3,5-dichlorophenyl)-N'-(1,1,2-trimethylpropyl)carbodiimide as an oil. To a solution of this oil in 20 ml of DMF were added 1.3 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 120° C. for 12 hours, cooled to room temperature and poured into 600 ml of water. The resulting crystals were collected by filtration and purified by silica gel column chromatography using chloroform as a solvent to yield 1.6 g of crude product. Recrystallization from benzene-cyclohexane mixture gave 1.2 g of the title compound as colorless platelets melting at 167.0°-170.0° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with petroleum ether
  4. customThe extract was evaporated in vacuo

Sources & evidence

ORD record
ord-f00968ed1ffc432ea283cf7661d5ea1a
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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