1-Hexanol → hexyl 1H-imidazole-1-carboxylate

HRID 1470523Notes

Reaction equation

HRID 1470523 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:8]1[N:12]=[CH:11][N:10]([C:13](N2C=NC=C2)=[O:14])[CH:9]=1>O1CCCC1>[N:10]1([C:13]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:14])[CH:9]=[CH:8][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 81031-HexanolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 57389745hexyl 1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

A solution of n-hexanol (30.6 g) in tetrahydrofuran (400 ml) was slowly added to solution of N,N-carbonyldiimidazole (55.08 g) in tetrahydrofuran (100 ml) and stirred for 2½ hour at 25-35° C. to provide hexyl 1H-imidazole-1-carboxylate compound of formula-4. 1-methyl-2-[N-[4-amidinophenyl]aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide compound of formula-5 (100 g), tetrahydrofuran (700 ml), water (800 ml) and potassium carbonate (138 g) were added to the reaction mixture and stirred for 20 hours at 25-30° C. After completion of the reaction, filtered the solid, washed with tetrahydrofuran and then dried to get title compound.

Sources & evidence

ORD record
ord-1f3ec84dd959445ca13114f2c103a1f5
Source dataset
uspto-grants-2015_04
Patent number
US09006448B2

Reaction notes

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