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Carbon Tetrachloride → HCID 50849909, compound

HRID 2041216
Notes
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Reaction equation

HRID 2041216 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-841d9a202ccd457f98003839a72cb214
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580780B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes