Carbon Tetrachloride → HCID 19910776, compound

HRID 1534106Notes

Reaction equation

HRID 1534106 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=S)[CH:5]=[C:6]([Br: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>[Br:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[N:12][C:13]([CH2:16][CH3:17])([CH3:14])[CH3:15])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020152HCID 15020152, compound

Product 1

HCID 19910776HCID 19910776, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.4 g of N-(3,5-dibromophenyl)-N'-t-pentylthiourea produced in Example A-10 in 55 ml of dichloromethane were added 3.3 g of triphenylphosphine, 2.0 g of carbon tetrachloride and 1.3 g of triethylamine. The mixture was refluxed for 4 hours and evaporated in vacuo. The residue was extracted with petroleum ether and the extract evaporated in vacuo to give N-(3,5-dibromophenyl)-N'-t-pentylcarbodiimide as an oil. To a solution of this oil in 20 ml of DMF were added 1.2 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 3 hours, cooled to room temperature and poured into 600 ml of water. The resulting crystals were collected, washed with a small amount of cyclohexane and recrystallized from ethanol to give 0.9 g of the title compound as colorless needles melting at 168.0°-170.0° C.

Workup

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

Sources & evidence

ORD record
ord-909ec9bf1ee24719a460fbb4f2f43728
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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