Carbon Tetrachloride → HCID 19910782, compound

HRID 1534101Notes

Reaction equation

HRID 1534101 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH2:17][CH3:18])([CH3:16])[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]([CH2:17][CH3:18])([CH3:16])[CH2:14][CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020148HCID 15020148, compound

Product 1

HCID 19910782HCID 19910782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.5 g of N-(3,5-dichlorophenyl)-N'-(1-ethyl-1-methylpropyl)thiourea produced in Example A-5 and 5.8 g of triphenylphosphine in 60 ml of dichloromethane were added 2.2 g of triethylamine and 3.4 g of carbon tetrachloride. The mixture was refluxed for 4 hours, cooled to room temperature and evaporated in vacuo. The residue was stirred with n-hexane and the resulting solid matter was removed by filtration. The filtrate was evaporated to give N-(3,5-dichlorophenyl)-N'-(1-ethyl-1-methylpropyl)carbodiimide as an oil. To a solution of this oil in 20 ml of DMF were added 3.4 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 40 minutes, cooled to room temperature and poured into water. The resulting crystals were filtered off and recrystallized from benzene to give 3.5 g of the title compound as colorless flakes melting at 148.0°-150.0° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customevaporated in vacuo
  3. customthe resulting solid matter was removed by filtration
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-aaac53bee23a44a1befbe66aed160d8f
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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