Benzyl chloroformate → 5,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-benzoimidazole-1-carboxylic acid benzyl ester

HRID 25498Notes

Reaction equation

HRID 25498 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CN(C)C=O>[CH2:29]([O:28][C:26]([N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[C:21]([Cl:22])=[CH:20][C:5]=2[N:6]=[C:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 225684155,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole

Product 1

HCID 698015975,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-benzoimidazole-1-carboxylic acid benzyl esterYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (25 mL) was added to 5,6-dichloro-2-(4-methoxy-3-nitro-phenyl)-1H-benzoimidazole (1.01 g, 3 mmol) from Step A. As the mixture stirred, sodium hydride (0.168 g, 4.2 mmol) was gradually added. After 3 hours, benzyl chloroformate (0.857 mL, 6 mmol) was added dropwise to the mixture. The reaction mixture was stirred overnight and then was partitioned between water (1,000 mL) and ethyl acetate (500 mL). The solvent was removed on the rotary evaporator and the residue triturated with 4:1 hexane:ethyl acetate to give the product (0.62 g), mp 212-214° C.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customwas partitioned between water (1,000 mL) and ethyl acetate (500 mL)
  3. customThe solvent was removed on the rotary evaporator
  4. customthe residue triturated with 4:1 hexane

Sources & evidence

ORD record
ord-209d0ea531274ba2a9f569c82703f6e2
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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