2-Aminobenzimidazole → N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 2257786Notes

Reaction equation

HRID 2257786 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].NC1[NH:15][C:16]2C=C[CH:20]=[CH:19][C:17]=2N=1>C(#N)C>[N:15]1[C:16]2[CH:17]=[CH:19][CH:20]=[CH:12][C:11]=2[NH:10][C:9]=1[NH:8][C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2]

Participants

4

Reactant 2

HCID 136242-AminobenzimidazoleHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamideYield 73.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1'-thiocarbonyldiimidazole (8.91 g, 50 mmol) and 2-aminobenzimidazole (6.66g, 50 mmol) in acetonitrile (50 mL) was stirred at room temperature for 19 hours. The resulting precipitate was collected by filtration to provide 8.92 g (73%) of the titled product: IR (KBr, cm-1) 3058, 2621, 1623, 1580, 1509, 1469, 1445, 1355, 1290, 1252, 1212, 1153, 1099, 1081, 1048, 925, 898, 746, 659; 1H NMR (300 MHz, DMSO-d6) δ 13.24 (br s, 2H), 8.52 (s, 1H), 7.87 (s, 1H), 7.57 (m, 2H), 7.33 (m, 2H), 6.96 (s, 1H); MS (FAB) m/e 244 (M+1); UV (EtOH) 351 nm (ε=18204), 283 nm (ε=13099), 227 nm (ε=17339), 204 nm (ε=31915).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-fe2622f347ae4de59c4bb20ec6f27e93
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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