Benzimidazole → Diisopropylethylamine

HRID 1804657Notes

Reaction equation

HRID 1804657 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-5840c29091c14ae581d8f866ebfbfeb9
Source dataset
uspto-grants-2013_01
Patent number
US08354419B2

Reaction notes

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