Benzimidazole → Diisopropylethylamine

HRID 1615098Notes

Reaction equation

HRID 1615098 reaction equation
[N:1]1[C:5]2[CH:6]=CC=C[C:4]=2N[CH:2]=1.[CH2:10]1[CH2:14]OC[CH2:11]1.[CH3:15]N(C=O)C>C(Cl)Cl>[CH3:15][CH2:2][N:1]([CH:10]([CH3:14])[CH3:11])[CH:5]([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 6228DimethylformamideHCID 8028Tetrahydrofuran

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The benzimidazole is formed by coupling the diamino compound with the appropriate carboxylic acid, preactivated carboxylic acid, mixed anhydride or anhydride in solvents such as THF, DMF or DCM and in the presence of a base such as TEA or DIPEA to form the corresponding amide. The amide is than treated with an acid at 40-80° C. for 2-24 hours.

Sources & evidence

ORD record
ord-ae6b2d06ca594c61be8df6cf3e5a3fec
Source dataset
uspto-grants-2014_07
Patent number
US08765731B2

Reaction notes

Loading…