2-Aminothiazole → HCID 178512080, compound

HRID 925025Notes

Reaction equation

HRID 925025 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[C:12](#[N:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:12](=[NH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 7505BenzonitrileHCID 178418339Butyllithium

Product 1

HCID 178512080HCID 178512080, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts and modifications: 5.01 g of 2-aminothiazole (50.0 mmol), 26.0 mL of 2.0 M butyllithium (52.0 mmol), 5.20 mL of benzonitrile (51.0 mmol). After refluxing overnight, the solution was green-brown. Addition of water yielded a red-brown solution with suspended solid. Solution was taken to dryness yielding 6.66 g (66%) of yellow-orange material. 1H NMR (400 MHz, C6D6): 10.1 (br, 1H), 7.68 (d, 2H), 7.34 (d, 1H), 7.04 (m, 3 H), 6.40 (d, 1H), 5.35 (br, 1H), 2.26 (s, 6H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a red-brown solution

Sources & evidence

ORD record
ord-bfb5f1bc833740859e466fd0ecee8063
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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