Water → HCID 67963110, compound

HRID 2172538Notes

Reaction equation

HRID 2172538 reaction equation
[C:1]1([S:7][CH:8](SC2C=CC=CC=2)[CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[N:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N12CCCN=C1CCCCC2.ClCCl.O>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([N:19]=[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][CH2:18]/[C:9]/2=[CH:8]\[S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86702348HCID 86702348, compound

Product 1

HCID 67963110HCID 67963110, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

266 mg (0.56 mmol) of N-{2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-ylidene}-4-fluoroaniline are dissolved in 50 ml of toluene, 0.26 ml (0.26 mmol of a titanium(IV) tetrachloride solution (1 M in dichloromethane) is added a little at a time at 25° C. and the mixture is stirred for 1 h. 431 mg (2.83 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 5 ml of dichloromethane are added, and this mixture is poured into water and extracted with ethyl acetate. After washing with saturated aqueous sodium chloride solution, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on RP18 (mobile phase: acetonitrile/water) gives 84 mg of 4-fluoro-N-[(2E)-2-[(phenylsulphanyl)methylene]-3,4-dihydronaphthalen-1(2H)-ylidene]aniline.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing with saturated aqueous sodium chloride solution
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography on RP18 (mobile phase: acetonitrile/water)

Sources & evidence

ORD record
ord-3f9230cae084454bacb7d3f562949a0e
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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