Methyl 3-phenyl-DL-alaninate hydrochloride → N-[(2-thiazolylamino)thioxomethyl]-DL-phenylalanine methyl ester

HRID 2257776Notes

Reaction equation

HRID 2257776 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](N1C=CN=C1)=[S:8].Cl.[CH3:15][O:16][C:17](=[O:27])[CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19]>CN(C)C=O>[CH3:15][O:16][C:17](=[O:27])[CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:19][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[S:8]

Participants

4

Reactant 2

HCID 3084017Methyl 3-phenyl-DL-alaninate hydrochlorideHCID 10750950N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 19704073N-[(2-thiazolylamino)thioxomethyl]-DL-phenylalanine methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-thiazolyl) thiocarbamoyl] imidazole (4.21 g, 20.0 mmol) and DL-phenylalanine methyl ester hydrochloride (4.31 g, 20.0 mmol) in N,N-dimethylformamide (150 mL) was heated at 90° C. for 3 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, recrystallized from ether-hexanes to provide 3.26 g (51%) of the titled product: IR (KBr, cm-1) 3184, 3029, 1735 1569, 1510, 1223, 1189; 1H NMR (300 MHz, DMSO-d6) δ 11.90 (s, 1H), 7.40 (d, 1H), 7.20-7.38 (m, 5H), 7.17 (d, 1H), 5.30 (q, 1H), 3.63 (s, 3H), 3.02 -3.22 (m, 2H); MS (FD) m/e 321 (M+); UV (EtOH) 291 nm (ε=18235), 255 nm (ε=10773), 202 nm (ε=20575). Anal. Calcd for C14H15N3O2S2 : C, 52.31; H, 4.70; N, 13.07. Found: C, 52.24; H, 4.61; N, 13.18.

Workup

  1. customsolvent removed under reduced pressure
  2. customrecrystallized from ether-hexanes

Sources & evidence

ORD record
ord-8d1a8b3d48474488a3455f104f305e93
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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