Carbon Tetrachloride → HCID 19910783, compound

HRID 1534105Notes

Reaction equation

HRID 1534105 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]([Br:16])[CH:10]=1)=S)([CH3:4])([CH3:3])[CH3:2].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>[C:1]([N:5]=[C:6]=[N:8][C:9]1[CH:10]=[C:11]([Br:16])[CH:12]=[C:13]([Br:15])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15020151HCID 15020151, compound

Product 1

HCID 19910783HCID 19910783, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.5 g N-t-butyl-N'-(3,5-dibromophenyl)thiourea produced in Example A-9 in 80 ml of dichloromethane were added 5.0 g of triphenylphosphine, 3.0 g of carbon tetrachloride and 1.9 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-t-butyl-N'-(3,5-dibromophenyl)carbodiimide as an oil. To a solution of this oil in 30 ml of DMF were added 1.9 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 4 hours, cooled to room temperature and poured into 700 ml of water. The resulting crystals were collected, washed with small amount of cyclohexane and recrystallized from benzene to give 2.0 g of the title compound as colorless needles melting at 189.0°-191.0° 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-786f1c3176f745b0a48a15a90775670f
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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