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Carbon Tetrachloride → HCID 50849909, compound

HRID 911328
Notes
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Reaction equation

HRID 911328 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:24])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:24][CH2:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:8][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 43237946-Methyl-2-phenylbenzothiazole

Product 1

HCID 50849909HCID 50849909, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

Combine 6-methyl-2-phenyl-benzothiazole (0.2 g, 0.98 mmol), NBS (0.2 g, 1.02 mmol), AIBN (20 mg, 0.10 mmol), carbon tetrachloride (5 mL) and reflux for 3 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, concentrate and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 8:2 and 7:3) to obtain the title compound as a white solid (0.2 g, 69%).

Workup

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. concentrationconcentrate
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 8:2 and 7:3)

Sources & evidence

ORD record
ord-37da182ad8544407a5feed07fe4e2e7f
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022062B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes