Phenethylamine → HCID 86750191, compound

HRID 2257770Notes

Reaction equation

HRID 2257770 reaction equation
[CH2:1]1[C:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]=2[S:3][N:2]1[NH:14][C:15]([N:17]1[CH:21]=[CH:20]N=C1)=[S:16])=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:22]1(CCN)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[C:22]1([CH2:20][CH2:21][NH:17][C:15]([NH:14][N:2]2[CH2:1][C:5]3[C:6]4[C:11]([CH:12]=[CH:13][C:4]=3[S:3]2)=[CH:10][CH:9]=[CH:8][CH:7]=4)=[S:16])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 86750190HCID 86750190, compound

Product 1

HCID 86750191HCID 86750191, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-naptho[1,2]thiazolyl)-thiocarbamoyl] imidazole (1.6 g, 5 mmol) and 2-phenylethylamine (0.62 g, 5.2 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 1 h, the reaction was cooled to room temperature and the solvent removed in vacuo. The residue was crystallized from ethyl acetate to provide 1.5 g (82%) of the titled product: IR (KBr, cm-1) 3171, 3027, 1581, 1521, 1213, 695; 1H NMR (300 MHz, DMSO-d6) δ 11.7 (br s, 1H), 9.9 (br s, 1H), 8.25 (d, J=8 Hz, 1H), 8.0 (d, J=8 Hz, 2H), 7.8 (d, J=8 Hz, 1H), 7.6-7.2 (m, 7H), 3.95 (m, 2H), 3.05 (t, J=7 Hz, 2H); MS (FD) m/e 364 (M+); UV (EtOH) 340 nm (ε=23922), 325 nm (ε=19262), 313 nm (ε=20808), 245 nm (ε=39665), 209 nm (ε=36141). Anal. Calcd for C20H17N3S2 : Theory: C, 66.09; H, 4.71; N, 11.56. Found: C, 65.86; H, 4.84; N, 11.48.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-355615c10c264f3a94e5f680e17a02b6
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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