Water → 1-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea

HRID 1823794Notes

Reaction equation

HRID 1823794 reaction equation
CO[C:3](=[O:15])[NH:4][C:5]1[NH:9][C:8]2[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:7]=2[N:6]=1.[CH3:16][O:17][CH2:18][CH2:19][NH2:20].O>CN1CCCC1=O>[OH:14][C:11]1[CH:12]=[CH:13][C:7]2[N:6]=[C:5]([NH:4][C:3]([NH:20][CH2:19][CH2:18][O:17][CH3:16])=[O:15])[NH:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80182-MethoxyethylamineHCID 115152Methyl 5-hydroxybenzimidazol-2-ylcarbamate

Product 1

HCID 221469461-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (6-hydroxy-1H-benzoimidazol-2-yl)-carbamic acid methyl ester (300 mg, example 61) and 2-methoxy-ethylamine (630 IA) in N-methylpyrrolidinone (8 ml) was heated at 90° C. in a sealed tube for 20 hours. The reaction mixture was poured into water (160 ml) and extracted three times with ethyl acetate (40 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 C:5 C, v/v) to 1-(6-hydroxy-1H-benzoimidazol-2-yl)-3-(2-methoxy-ethyl)-urea as a yellow solid (180 mg). Mass spectrum: 251 [M+H]+; retention time=0.55 minutes.

Workup

  1. extractionextracted three times with ethyl acetate (40 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95 C:5 C, v/v) to 1-(6-hydroxy-1H-benzoimidazol-2-yl)-3-(2-methoxy-ethyl)-urea as a yellow solid (180 mg)

Sources & evidence

ORD record
ord-088b458c0dc74deda47a30403eb7bdf6
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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