Dichloromethane → HCID 86702347, compound

HRID 2172541Notes

Reaction equation

HRID 2172541 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](C)=[CH:4][CH:3]=1.[C:9]1([S:15][CH:16]([S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N12CCCN=C1CCCCC2.ClCCl>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.O>[C:9]1([S:15][CH:16]([S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[N:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7813p-ToluidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86702351HCID 86702351, compound

Product 1

HCID 86702347HCID 86702347, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 341 mg (3.19 mmol) of p-toluidine are added to 400 mg (1.06 mmol) of 2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-one in 20 ml of toluene. After cooling to 0° C., 0.53 ml (0.53 mmol) of a titanium(IV) tetrachloride solution (1 M in dichloromethane) is added slowly. After 1 h of stirring at 0° C. and a further 1 h at 25° C., 809 mg (5.31 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 5 ml of dichloromethane are added. 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 silica gel (mobile phase: cyclohexane/ethyl acetate) gives 298 mg of N-{2-[bis(phenylsulphanyl)methyl]-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 silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-8714e189a7b345feb48ab9ad71363486
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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