N-bromobutanimide → HCID 68294245, compound

HRID 1472775Notes

Reaction equation

HRID 1472775 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH3:20])=[C:4]([CH3:21])[CH:3]=1.C1C(=O)N([Br:29])C(=O)C1.CC([O-])=O.[Na+]>CC(O)=O.C(Cl)Cl>[Br:29][C:10]1[S:11][C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH3:20])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:21])[N:9]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 517045Sodium AcetateHCID 68293844HCID 68293844, compound

Product 1

HCID 68294245HCID 68294245, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4,5-Bis(4-chloro-2-methylphenyl)thiazole (170 mg, 0.51 mmol), NBS (100 mg, 0.56 mmol) and NaOAc (82 mg, 1.0 mmol) in AcOH (5 mL) and DCM (3 mL) was stirred overnight at rt, and then quenched with water (25 mL) and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography to afford 196 mg of product.

Workup

  1. customquenched with water (25 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-156ad80ca9e344dfa566bb480ec8101f
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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