Chloroform → 5-bromo-2-(N-ethyl-2,4-dichloroanilino)-4-methylthiazole

HRID 23550

Reaction equation

HRID 23550 reaction equation
Cl.[CH2:2]([N:4]([C:13]1[S:14][CH:15]=[C:16]([CH3:18])[N:17]=1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])[CH3:3].C(=O)([O-])[O-].[Ca+2].C(Cl)(Cl)Cl.[Br-:28].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>CO>[Br:28][C:15]1[S:14][C:13]([N:4]([CH2:2][CH3:3])[C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=2[Cl:12])=[N:17][C:16]=1[CH3:18]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10112Calcium CarbonateHCID 225744262-(N-ethyl-2,4-dichloroanilino)-4-methylthiazole hydrochlorideHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 121346655-bromo-2-(N-ethyl-2,4-dichloroanilino)-4-methylthiazoleYield 117.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 2-(N-ethyl-2,4-dichloroanilino)-4-methylthiazole hydrochloride (6.0 g) and calcium carbonate (4.6 g) were suspended in a mixed solvent of chloroform (90 mL) and methanol (36 mL), benzyl-trimethylammonium tribromide (7.2 g) was added thereto in small portions. The solids in the reaction mixture were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=9:1) to obtain 5-bromo-2-(N-ethyl-2,4-dichloroanilino)-4-methyl-thiazole (4.5 g).

Workup

  1. additionwas added
  2. filtrationThe solids in the reaction mixture were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=9:1)

Sources & evidence

ORD record
ord-34198016cd934b30945836604352d606
Source dataset
uspto-grants-2005_02
Patent number
US06852732B2

Linked notes

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