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2-Isopropylaniline → 2,2'-Dithiobis[N-[2-(1-methylethyl)phenyl]benzamide]

HRID 3733
Notes
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Reaction equation

HRID 3733 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].[CH:21]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26])([CH3:23])[CH3:22]>ClCCl.N1C=CC=CC=1>[CH3:22][CH:21]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH:26][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:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[CH:21]([CH3:23])[CH3:22])=[O:13])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 125612-IsopropylanilineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 189352932,2'-Dithiobis[N-[2-(1-methylethyl)phenyl]benzamide]Yield 14.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the general method of Example 90 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-isopropylaniline (1.60 g, 11.6 mmol) in 13 mL of pyridine. The crude product was recrystallized twice from acetonitrile-DMF to yield 0.45 g of the title compound, mp 235°-237° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized twice from acetonitrile-DMF

Sources & evidence

ORD record
ord-0d887acf58894cdeab531ebdbbaba9ed
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05734081

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes