2-Aminothiazole → HCID 86748184, compound

HRID 1737083Notes

Reaction equation

HRID 1737083 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:11][CH2:12][CH3:13])(=[O:10])[C:8]#[CH:9]>ClCCl.CN(C)C=O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1]/[CH:9]=[CH:8]/[C:7]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 21552-AminothiazoleHCID 12182Ethyl propiolate

Product 1

HCID 86748184HCID 86748184, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.3 g of 2-aminothiazole and 1.55 ml of ethyl propiolate in 10 ml of dichloromethane and 5 ml of dimethylformamide was stirred at ambient temperature for 3 days. The resulting mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel using first 20% then 40% ethyl acetate in hexane to provide 1.54 g (51%) of the desired compound. 1H NMR (CDCl3) δ 1.30 (t, J=7 Hz, 3 H), 4.22 (q, J=7 Hz, 2 H), 5.79 (d, J=15 Hz, 1 H), 6.03 (d, J=5 Hz, 1 H), 6.68 (d, J=5 Hz, 1 H), 7.47 (br, 1 H), 8.17 (d, J=15 Hz, 1 H). Mass spectrum: (M+H)+ =199.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed on silica gel using first 20%

Sources & evidence

ORD record
ord-48847c389093459bba7ec2971a05000d
Source dataset
uspto-grants-1996_07
Patent number
US05541334

Reaction notes

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