Glycolic Acid → (5-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanol

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[CH:6][CH:7]=1.[C:11]([OH:15])(=O)[CH2:12]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH3:9])[C:12]([CH2:11][OH:15])=[N:10][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 6407014-chloro-N1-methylbenzene-1,2-diamine

Product 1

HCID 4066944(5-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanolYield 45%

Conditions

Temperature: 150 °C

Procedure

4-chloro-N1-methylbenzene-1,2-diamine (15.0 g, 96 mmol) and glycolic acid (8.1 g, 106 mmol) were mixed together in a sealed tube. The mixture was heated at 150° C. for 5 hours before it was cooled down to room temperature. The residue was purified by flash column chromatography (0-5% MeOH in CH2Cl2) to give the product (8.5 g, 45% yield). 1H NMR (300 MHz, CDCl3) δ: 3.80 (s, 3H), 4.86 (s, 2H), 7.13-7.22 (m, 2H), 7.62-7.64 (m, 1H).

Workup

temperaturewas cooled down to room temperature
customThe residue was purified by flash column chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-8900456556e142108daa4a5653330f99
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

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