Dichloromethane → HCID 53863236, compound

HRID 704336Notes

Reaction equation

HRID 704336 reaction equation
[C:1]1([C:7]([NH:15][C:16](=O)[C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)[Cl:42]>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]([N:15]=[C:16]([Cl:42])[C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11776Triphenylphosphine2×HCID 53990749HCID 53990749, compound

Product 1

HCID 53863236HCID 53863236, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

18.4 g of the product of Step A were refluxed for 4 hours in 320 ml of methylene chloride, 18.22 g of triphenylphosphine and 6.7 ml of carbon tetrachloride. 9.11 g of triphenylphosphine in 3.35 ml of carbon tetrachloride were added without reflux and after heating for a further one hour at reflux, the mixture stood for 16 hours at ambient temperature. The solvents were expelled under reduced pressure and the residue was triturated in a 1-1 mixture of ether and methylene chloride, then separated. The filtrate was concentrated under reduced pressure and the residue was chromatographed on silica and eluted with methylene chloride to obtain 18.7 g of the expected product.

Workup

  1. temperaturewithout reflux
  2. temperatureafter heating for a further one hour
  3. temperatureat reflux
  4. customthe residue was triturated in a 1-1 mixture of ether and methylene chloride
  5. customseparated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was chromatographed on silica
  8. washeluted with methylene chloride

Sources & evidence

ORD record
ord-9fc6d2cf398f4767a6e44d1f8bd0cb20
Source dataset
uspto-grants-1991_01
Patent number
US04987140

Reaction notes

Loading…