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

HRID 630133Notes

Reaction equation

HRID 630133 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]([C:12](=O)[CH:13]([CH3:15])[CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH4+].[OH-]>C(O)C>[NH2:1][C:2]1[S:3][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([CH:13]([CH3:15])[CH3:14])[N:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723790ThioureaHCID 13015595Ethyl 2-bromo-4-methyl-3-oxopentanoate

Product 1

HCID 824436Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylateYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a refluxing solution of thiourea (1.9 g, 25.6 mmol) in absolute ethanol (20 mL) was added ethyl 2-bromo-4-methyl-3-oxopentanoate (6.0 g, 25.3 mmol). The solution was stirred at reflux for another 1.5 hours. After cooling to room temperature, the solution was poured in ice/water (100 mL). The mixture was neutralized with concentrated NH4OH. The solid material was recovered by filtration, washed with water (2×20 mL) and hexanes (2×20 mL), and dried in vacuo, affording ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylate (3.6 g, 66% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for another 1.5 hours
  2. filtrationThe solid material was recovered by filtration
  3. washwashed with water (2×20 mL) and hexanes (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-410d14fa27b041738e27adb1a732b1e8
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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