Dichloroacetic Acid → 4,5-Dimethyl-1H-benzo[d]imidazole-2-carbaldehyde

HRID 536107Notes

Reaction equation

HRID 536107 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].Cl[CH:12](Cl)[C:13](O)=[O:14]>Cl>[CH3:1][C:2]1[C:3]2[N:10]=[C:12]([CH:13]=[O:14])[NH:9][C:4]=2[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 5210773,4-Dimethylbenzene-1,2-diamine

Product 1

HCID 451207614,5-Dimethyl-1H-benzo[d]imidazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3,4-Dimethylbenzene-1,2-diamine (0.409 g, 3.0 mmol) and dichloroacetic acid (0.768 g, 6.0 mmol) in 4N HCl (10 mL) were heated at 100° C. for two days. After cooling to r.t. the mixture was filtrated and the mother liquor was extracted with chloroform (4 times). The pH was set to 12 using 2M NaOH and the resulting white precipitate was collected by filtration. The crude product was used in the next step without further purification.

Workup

  1. filtrationwas filtrated
  2. extractionthe mother liquor was extracted with chloroform (4 times)
  3. filtrationthe resulting white precipitate was collected by filtration
  4. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-f351a5b6600444d895edd081eaf656a2
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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