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

HRID 630272Notes

Reaction equation

HRID 630272 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 added ethyl 2-bromo-3-oxopentanoate (7.3 g, 32.7 mmol) always keeping the mixture at reflux. The solution was stirred at reflux for another 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
  2. temperatureat reflux for another 1.5 hours
  3. filtrationThe solid material was recovered by filtration
  4. washwashed with water (2×50 mL) and hexanes (3×50 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ff207bffecdc4b21b66ad1fd8bd58ab1
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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