O-Toluidine → HCID 18935294, compound

HRID 1378816Notes

Reaction equation

HRID 1378816 reaction equation
[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[C:23]([CH3:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>ClCCl.N1C=CC=CC=1>[CH3:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:1](=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[O:13]

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 18935294HCID 18935294, compoundYield 3.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and o-toluidine (1.25 g, 11.7 mmol) in 10 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol and recrystallized from acetonitrile-DMF to yield 0.11 g of the title compound, mp 224°-225° C (dec.).

Workup

  1. customThis compound was prepared
  2. customThe crude product was triturated with a hot mixture of ethyl acetate and ethanol
  3. customrecrystallized from acetonitrile-DMF

Sources & evidence

ORD record
ord-ce000b2309634be290aa26a2bfb4309a
Source dataset
uspto-grants-1997_09
Patent number
US05668291

Reaction notes

Loading…