Ammonium Hydroxide → Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylate

HRID 250236Notes

Reaction equation

HRID 250236 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6](=O)[CH:7]([CH3:9])[CH3:8])[CH3:2].[NH2:12][C:13]([NH2:15])=[S:14].[NH4+].[OH-]>ClCCl>[CH2:1]([O:3][C:4]([C:5]1[S:14][C:13]([NH2:15])=[N:12][C:6]=1[CH:7]([CH3:9])[CH3:8])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 81583Ethyl isobutyrylacetateHCID 2723790Thiourea

Product 1

HCID 824436Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-3-oxo-pentanoic acid ethyl ester (10 g, 63.2 mmol) in dichloromethane (150 mL) at 0° C. is added SO2Cl2 (5.64 mL, 69.5 mmol). The reaction mixture is stirred at ambient temperature for 1 hour. The reaction mixture is extracted with water (30 mL). To the aqueous layer is added 1,4-dioxane (60 mL) followed by thiourea (8.8 g, 63.2 mmol). The mixture is stirred at 80° C. overnight and cooled to room temperature. The reaction mixture is adjusted to pH 12 with conc. NH4OH and filtered. The filter cake is washed with water to give the title compound (12.4 g, 92%).

Workup

  1. extractionThe reaction mixture is extracted with water (30 mL)
  2. additionTo the aqueous layer is added 1,4-dioxane (60 mL)
  3. stirringThe mixture is stirred at 80° C. overnight
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. washThe filter cake is washed with water

Sources & evidence

ORD record
ord-c1b0fda251fc4c1ab299f85a1b6b9cfd
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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