2-Aminothiazole → HCID 58111428, compound

HRID 58266Notes

Reaction equation

HRID 58266 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].[Br:7][CH:8]([CH3:16])[C:9](=O)[CH2:10][C:11](OC)=[O:12]>>[Br:7][CH:8]([C:9]1[N:6]=[C:2]2[S:1][CH:5]=[CH:4][N:3]2[C:11](=[O:12])[CH:10]=1)[CH3:16]

Participants

3

Reactant 2

HCID 21552-AminothiazoleHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 58111428HCID 58111428, compound

Conditions

Temperature
110 °C

Procedure

A mixture of polyphosphoric acid (73.8 g, 677 mmol), 1,3-thiazol-2-amine (12.3 g, 123 mmol), and methyl 4-bromo-3-oxopentanoate (34.8 g, 166 mmol) was stirred at 110° C. overnight. After cooling, an ice-cold 10% aq. NaOH solution was slowly added to adjust the pH to 7. The mixture was filtered, and the collected precipitate was air-dried to give crude product which was directly used in next step. LCMS calculated for C8H8BrN2OS (M+H)+: m/z=259.0. Found: 259.0.

Workup

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. customthe collected precipitate was air-dried
  4. customto give crude product which

Sources & evidence

ORD record
ord-92f53ceabd6d4381b252a49e4df22896
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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