Chlorosuccinimide → HCID 59498104, compound

HRID 2061014Notes

Reaction equation

HRID 2061014 reaction equation
[C:1]1([S:7][CH:8]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClN1C(=O)CCC1=O>C1(C)C=CC=CC=1>[C:26]1([S:25][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][C:10]([S:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 25206561HCID 25206561, compound

Product 1

HCID 59498104HCID 59498104, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.50 g (1.1 mmol) of phenyl 3,3-bis(phenylthio)-N-(phenyl)propanimidothioate in toluene (5 mL) was added 0.16 g (1.2 mmol) of N-chlorosuccinimide under ice cooling and stirred at room temperature for 3 hours. After dilution with t-butyl methyl ether (50 mL), the mixture was washed with saturated NaCl solution, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 38 mg of phenyl 3,3-bis(phenylthio)-N-phenyl-2-propenimidothioate (hereinafter referred to as the present compound 45).

Workup

  1. washAfter dilution with t-butyl methyl ether (50 mL), the mixture was washed with saturated NaCl solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-0364e46c99354073b4e4206b9109d70b
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

Loading…