1-Hydroxybenzotriazole → 1,2-Dimethylbenzimidazole

HRID 2287556Notes

Reaction equation

HRID 2287556 reaction equation
NCC(N(C1C(Cl)=C(C(Cl)=CC=1)CO[C:12]1[C:20]2[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=2[CH:15]=[CH:14][CH:13]=1)C)=O.CNC(C1C=CC(C=CC(O)=O)=CC=1)=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O>[CH3:22][N:17]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:20]=2[N:19]=[C:18]1[CH3:21]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 154621764-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazoleHCID 534120223-[4-(Methylcarbamoyl)phenyl]prop-2-enoic acid

Product 1

HCID 3126931,2-DimethylbenzimidazoleYield 337.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole (100 mg), 4-(methylcarbamoyl)cinnamic acid (55.4 mg) and dimethylformamide (1 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (61.2 mg) and 1-hydroxybenzotriazole (49.7 mg), and the mixture was stirred for 3 hours at ambient temperature. To the mixture was added water, and the mixture was extracted with dichloromethane. The separated organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (dichloromethane-methanol) to give 4-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]benzyloxy]]-1,2-dimethyl-1H-benzimidazole (121 mg).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe separated organic layer was washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-9859af679dcd4eda823c0c64825cf3c1
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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