2-Aminothiazole → HCID 59408742, compound

HRID 1188112Notes

Reaction equation

HRID 1188112 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:7]=O)=[CH:5][N:6]=1.[NH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.CCO>[Br:1][C:2]1[S:3][C:4]([CH2:7][NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59408742HCID 59408742, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-bromothiazole-5-carbaldehyde (150 mg, 0.78 mmol) and 2-amino-thiazole (78 mg, 0.78 mmol) in toluene (7 mL) and 3 Å molecules sieves were stirred at reflux overnight. The strong yellow solution of the corresponding imine was then poured over NaBH4 (147 mg, 3.9 mmol) in hot EtOH (50 mL). The colorless solution was filtered, concentrated and purified by column chromatography (30% AcOEt/PE) yielding N-((2-bromothiazol-5-yl)methyl)thiazol-2-amine (110 mg, 51%) as a solid.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe colorless solution was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography (30% AcOEt/PE)

Sources & evidence

ORD record
ord-046e6d3a55c143d08b9b889981ad5ba6
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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