Carbon Tetrachloride → HCID 19910788, compound

HRID 1534107Notes

Reaction equation

HRID 1534107 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)=S)([CH3:4])([CH3:3])[CH3:2].ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(N(CC)CC)C>[C:1]([N:5]=[C:6]=[N:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 15020153HCID 15020153, compound

Product 1

HCID 19910788HCID 19910788, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.04 g of N-t-butyl-N'-(3-chloro-5-fluorophenyl)thiourea produced in Example A-11 in 25 of dichloromethane were added 4.18 g of triphenylphosphine, 2.53 g of carbon tetrachloride and 1.61 g of triethylamine. The mixture was refluxed for 2 hours and evaporated in vacuo. The residue was chromatographed on a silica gel column using cyclohexane as a solvent to give N-t-butyl-N'-(3-chloro-5-fluorophenyl)carbodiimide as an oil. To a solution of this oil in 1.5 ml of DMF were added 500 mg of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 100° C. overnight, cooled to room temperature, poured into ice-water, and extracted with ethyl acetate. The extract was evaporated in vacuo to dryness and the residue recrystallized from isopropyl alcohol to give 0.1 g of the title compound as colorless needles melting at 156.0°-157.0° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-588a9224671441508cdb9e87002ea4d2
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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