O-Phenylenediamine → 4-((1H-Benzo[D]imidazol-2-YL)methyl)phenol

HRID 410165Notes

Reaction equation

HRID 410165 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](OC)=O)=[CH:4][CH:3]=1.[C:13]1([NH2:20])[C:14]([NH2:19])=[CH:15][CH:16]=[CH:17][CH:18]=1>CO>[NH:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:20]=[C:9]1[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 3939864-((1H-Benzo[D]imidazol-2-YL)methyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 2-(4-hydroxyphenyl)acetate (40.0 g, 241 mmol) and benzene-1,2-diamine (26.0 g, 241 mmol) in a sealed vessel was heated to 150° C. for 18 h. After cooling to room temperature, the mixture was diluted with MeOH and heated to 100 C for 1 h. The mixture was cooled to −20 C overnight, then filtered to collect 25.8 g (48%) of a lavender solid. MS (ESI, pos. ion) m/z: 225 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureheated to 100 C for 1 h
  3. temperatureThe mixture was cooled to −20 C overnight
  4. filtrationfiltered
  5. customto collect 25.8 g (48%) of a lavender solid

Sources & evidence

ORD record
ord-6b25f92adbee4a7f9c665df2b87e7696
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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