1,1'-Thiocarbonyldiimidazole → HCID 86750190, compound

HRID 2257769Notes

Reaction equation

HRID 2257769 reaction equation
[C:1]([N:8]1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].N[N:14]1[CH2:18][C:17]2[C:19]3[C:24]([CH:25]=[CH:26][C:16]=2[S:15]1)=[CH:23][CH:22]=[CH:21][CH:20]=3>C(#N)C>[CH2:18]1[C:17]2[C:19]3[C:24]([CH:25]=[CH:26][C:16]=2[S:15][N:14]1[NH:8][C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2])=[CH:23][CH:22]=[CH:21][CH:20]=3

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 69717629HCID 69717629, compound

Product 1

HCID 86750190HCID 86750190, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1'-thiocarbonyldiimidazole (1.8 g, 20 mmol) and 2-aminonaptho[1,2]thiazole (2.0 g, 20 mmol) in acetonitrile (150 mL) was stirred at 65° C. for 24 h. The resulting precipitate was collected by filtration to provide 1.69 g (46%) of the titled product. IR (KBr, cm-1) 3148, 2670, 1465, 736; 1H NMR (300 MHz, DMSO-d6) δ 9.2 (s, 1H ) 8.85 (s, 1H ), 8.65 (d, J=8 Hz, 1H), )8.2 (br s, 1H), 8.0-7.3 (m, 5H); MS (FD) m/e 309 (M+ -H); UV (EtOH) 383nm (e=8297), 244 nm (e=15160), 226 nm (ε=17126). Anal. Calcd for C15H10N4S2 : Theory: C, 58.04; H, 3.25; N, 18.05. Found: C, 58.13; H, 3.21; N, 18.03.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-1220cebfc92d4a4eb0afd7107c6fe49e
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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