Water → HCID 22147021, compound

HRID 1823784Notes

Reaction equation

HRID 1823784 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([O:28][CH3:29])[C:23]([O:26][CH3:27])=[CH:24][CH:25]=1.O>CN1CCCC1=O>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 227703,4-DimethoxyanilineHCID 22147082HCID 22147082, compound

Product 1

HCID 22147021HCID 22147021, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-benzyl-2-chloro-3H-benzoimidazol-5-ol (250 mg) and 4-amino veratrole (296 mg) in N-methylpyrrolidinone (3 ml) was heated at 150° C. in a sealed tube for 4 hours then allowed to cool. The reaction mixture was then poured into water (30 ml) and extracted three times with ethyl acetate (30 ml). The combined extracts were dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5, v/v) to give 3-benzyl-2-(3,4-dimethoxy-phenylamino)-3H-benzoimidazol-5-ol (141 mg) as a yellow solid. Mass spectrum: 376 [M+H]+ retention time: 3.44 minutes.

Workup

  1. temperatureto cool
  2. extractionextracted three times with ethyl acetate (30 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5

Sources & evidence

ORD record
ord-9d9890b0820547ac91a16a10e53ebc39
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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