m-Chloroperbenzoic acid → HCID 67814911, compound

HRID 2172537Notes

Reaction equation

HRID 2172537 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][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[C:1]1([S:7]/[CH:8]=[C:9]2/[C:10](=[N:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:11]3[C:16]([CH2:17][CH2:18]/2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86702347HCID 86702347, compound

Product 1

HCID 67814911HCID 67814911, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

270 mg (0.58 mmol) of N-{2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-ylidene}aniline are dissolved in 25 ml of dichloromethane, 157 mg (0.64 mmol) of 70 percent strength meta-chloroperbenzoic acid are added at 0° C. and the mixture is stirred at 0° C. for 1 h. The mixture is then diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by preparative HPLC (RP18, mobile phase: acetonitrile/water) gives 45 mg of N-[(2E)-2-[(phenylsulphanyl)methylene]-3,4-dihydronaphthalen-1(2H)-ylidene]aniline.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by preparative HPLC (RP18, mobile phase: acetonitrile/water)

Sources & evidence

ORD record
ord-e01ee383f14b4a79bb1a16817c082375
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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