Ammonium Hydroxide → Ethyl 2-amino-4-ethyl-1,3-thiazole-5-carboxylate

HRID 630266Notes

Reaction equation

HRID 630266 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]([C:12](=O)[CH2:13][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]([CH2:13][CH3:14])[N:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723790ThioureaHCID 13048353Ethyl 2-bromo-3-oxopentanoate

Product 1

HCID 12801682Ethyl 2-amino-4-ethyl-1,3-thiazole-5-carboxylateYield 103.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a refluxing solution of thiourea (2.6 g, 34.3 mmol) in absolute ethanol (30 mL) was slowly added at reflux ethyl 2-bromo-3-oxopentanoate (7.3 g, 32.7 mmol). The solution was stirred at reflux for 1.5 hours. After cooling to room temperature, the solution was poured in ice/water (150 mL). The mixture was neutralized with concentrated NH4OH. The solid material was recovered by filtration, washed with water (2×50 mL) and hexanes (3×50 mL), and dried in vacuo, affording ethyl 2-amino-4-ethyl-1,3-thiazole-5-carboxylate (6.8 g, 94% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationThe solid material was recovered by filtration
  3. washwashed with water (2×50 mL) and hexanes (3×50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e39a12b85b014304b189839b3b63b8b6
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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