Chloroform → 5-Amino-2-(4-chloro-2-methoxyphenyl)-4-methylthiazole

HRID 1498942Notes

Reaction equation

HRID 1498942 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[O:20][CH3:21])=[N:10][C:9]=1[CH3:22])(C)(C)C.Cl.O1CCOCC1.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[O:20][CH3:21])=[N:10][C:9]=1[CH3:22]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 68641711[2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid tert-butyl ester

Product 1

HCID 686418935-Amino-2-(4-chloro-2-methoxyphenyl)-4-methylthiazoleYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (25 ml), [2-(4-chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid tert-butyl ester (1.02 g, 2.87 mmol) prepared in the Step 28-1-1 was dissolved, and a 4-N hydrogen chloride-dioxane solution (25 ml) was added thereto. The mixture was stirred at a room temperature for 16 hours. Chloroform was added to the mixture, and the resulting mixture was neutralized with a saturated sodium bicarbonate solution. The resulting mixture was subjected to extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (474 mg, 65%) as a light-brown powder.

Workup

  1. dissolutionwas dissolved
  2. extractionThe resulting mixture was subjected to extraction with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-2706ca54e753446ca5f1b61630640972
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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