Dimethylformamide → 2-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carbonyl chloride

HRID 1750201Notes

Reaction equation

HRID 1750201 reaction equation
[CH:1]1([CH2:6][C:7]2[N:11]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:10]3[CH:17]=[CH:18][C:19]([C:21]([OH:23])=O)=[CH:20][C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.C(Cl)(=O)C([Cl:32])=O>ClCCl>[CH:1]1([CH2:6][C:7]2[N:11]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:10]3[CH:17]=[CH:18][C:19]([C:21]([Cl:32])=[O:23])=[CH:20][C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86714413HCID 86714413, compound

Product 1

HCID 867143812-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8.00 g of 2-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid in 100 ml of dichloromethane 0.1 ml of DMF and 4 ml of oxalyl chloride were added. The reaction was stirred at it for 16 h, then concentrated and co-distilled with toluene to obtain 8.45 g (100%) of the crude product as a brown solid, which was used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-65e4af7b3ba14dc0a41753504dfe2a48
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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