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

HRID 1373091Notes

Reaction equation

HRID 1373091 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), benzyltrimethylammonium 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-methylthiazole (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-ca67bfb4a7af450ea5c6af2a7346fd03
Source dataset
uspto-grants-2007_01
Patent number
US07160900B2

Reaction notes

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