2-Isopropylaniline → HCID 178438961, compound

HRID 388942Notes

Reaction equation

HRID 388942 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:4]=2[N:3]=1.ClC1NC2C=CC=CC=2N=1.[CH:24]([C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29])([CH3:26])[CH3:25]>CN1C(=O)CCC1.O>[CH:24]([C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:4]=2[N:3]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 125612-IsopropylanilineHCID 785722-ChlorobenzimidazoleHCID 178526482HCID 178526482, compound

Product 1

HCID 178438961HCID 178438961, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2-chloro-5-nitro-1H-benzimidazole (1.5 mmol; prepared from nitration of 2-chloro-1H-benzimidazole; Galy et al, J. Heterocycl. Chem. 1997, 34, 6, 1781-1788) in dry NMP (3 mL) was added 2-isopropylaniline (4 mmol). The resulting solution was subjected to microwave irradiation at 150° C. for 1 h. The contents were cooled to room temperature, diluted with water (20 mL) and extracted with EtOAc (2×15 mL). The combined extracts were then washed with water (20 mL) and brine (20 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue obtained was purified by silica gel chromatography using EtOAc/hexane as eluent to obtain (2-isopropylphenyl)-(5-nitro-1H-benzimidazol-2-yl)-amine as light yellow solid.

Workup

  1. customirradiation at 150° C. for 1 h
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined extracts were then washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue obtained
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-a350f80c87904875a96789269be28b53
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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