Carbon Tetrachloride → HCID 19910775, compound

HRID 1534108Notes

Reaction equation

HRID 1534108 reaction equation
[Cl: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]([F: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]([CH2:16][CH3:17])([CH3:14])[CH3:15])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020154HCID 15020154, compound

Product 1

HCID 19910775HCID 19910775, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.5 g of N-(3-chloro-5-fluorophenyl)-N'-t-pentylthiourea produced in Example A-12 in 20 ml of dichloromethane were added 7.4 g of triphenylphosphine, 4.9 g of carbon tetrachloride and 2.85 g of triethylamine. The mixture was refluxed for 2 hours and evaporated in vacuo. The residue was extracted with petroleum ether and the extract was evaporated in vacuo to give N-(3-chloro-5-fluorophenyl)-N'-t-pentylcarbodiimide as an oil. To a solution of this oil in 20 ml of DMF were added 1.31 g of cyanamide and 2 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 15 hours, cooled to room temperature, poured into ice-water and extracted with ethyl acetate. The extract was evaporated in vacuo. The residue was chromatographed on a silica gel column using chloroform as a solvent and recrystallized from isopropyl alcohol to give 1.0 g of the title compound as colorless needles melting at 130°-131.0° C.

Workup

  1. temperatureThe mixture was refluxed for 2 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-9d2a406ec4714e68b9915593f26d98d6
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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