Ammonia → 1-Isopropyl-2-chloromethylbenzimidazole

HRID 620028Notes

Reaction equation

HRID 620028 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:3])[CH3:2].[Cl:12][CH2:13][C:14](O)=O.N>Cl>[CH:1]([N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]=[C:14]1[CH2:13][Cl:12])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 300Chloroacetic AcidHCID 105587871-N-(propan-2-yl)benzene-1,2-diamine

Product 1

HCID 212484181-Isopropyl-2-chloromethylbenzimidazoleYield 64.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-isopropyl-o-phenylenediamine (2.8 g, 18.6 mmol), which is a known compound, was reacted with monochloroacetic acid (2.64 g, 28 mmol) in hydrochloric acid. The reaction mixture was made to weak by alkaline alkali with aqueous ammonia and the obtained oily material was refined in a usual manner to give the title intermediate (2.5 g, 12 mmol).

Sources & evidence

ORD record
ord-9a9dcfe126da47e186ba1a05709c8a76
Source dataset
uspto-grants-1989_04
Patent number
US04818761

Reaction notes

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