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

HRID 2257777Notes

Reaction equation

HRID 2257777 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](N1C=CN=C1)=[S:12].Cl.[CH3:19][O:20][C:21](=[O:31])[CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:23]>CN(C)C=O>[CH3:19][O:20][C:21](=[O:31])[CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:23][C:11]([NH:10][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[S:12]

Participants

4

Reactant 2

HCID 3084017Methyl 3-phenyl-DL-alaninate hydrochlorideHCID 19703709N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 19703398N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl esterYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-benzothiazolyl) thiocarbamoyl] imidazole (1.30 g, 5.0 mmol) and DL-phenylalanine methyl ester hydrochloride (1.08 g, 5.0 mmol) in N,N-dimethylformamide (50 mL) was heated at 90° C. for 3 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, recrystallized from ethyl ether-hexanes to provide 1.31 g (70%) of the titled product: mp 168°-169° C.; IR (KBr, cm-1) 3168, 3030, 1732, 1548, 1525, 1206, 1193; 1H NMR (300 MHz, DMSO-d6) δ 10.30 (br s, 1H), 7.88 (d, 1H), 7.62 (d, 1H), 7.32 (t, 1H), 7.20-7.29 (m, 6H), 5.18 (q, 1H), 3.70 (s, 3H), 3.22 (m, 2H); MS (FD) m/e 371 (M+); UV (EtOH) 303 nm (ε=25329), 247 nm (ε=12095), 203 nm (ε=28990). Anal. Calcd for C18H17N3O2S2 : C, 58.20; H, 4.61; N, 11.31. Found: C, 58.19; H, 4.70; N, 11.30.

Workup

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

Sources & evidence

ORD record
ord-0ccd42b9b54f41ad8ef9561c12adfcc5
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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