Carbon Tetrachloride → HCID 19910786, compound

HRID 1534099Notes

Reaction equation

HRID 1534099 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][CH3:16])=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])[CH2:14][CH2:15][CH3:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020146HCID 15020146, compound

Product 1

HCID 19910786HCID 19910786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.0 g of N-(3,5-dichlorophenyl)-N'-(1,1-dimethylbutyl)thiourea produced in Example A-3 in 50 ml of dichloromethane were added 5.2 g of triphenylphosphine, 3.1 g of carbon tetrachloride and 2.0 g of triethylamine. The mixture was refluxed for 6 hours, and then 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-dimethylbutyl)carbodiimide as an oil. To a solution of this oil in 20 ml of DMF were added 1.6 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 6 hours, cooled to room temperature and poured into 400 ml of water. The resulting crystals were filtered off, washed with small amount of cyclohexane, and purified by silica gel column chromatography using chloroform as a solvent to give 1.2 g of the title compound. Recrystallization from cyclohexane gave 1.1 g of colorless platelets melting at 115.0°-117.0° C.

Workup

  1. temperatureThe mixture was refluxed for 6 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-b074edda25a243e4b570c0e45618df58
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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