Triethyl orthoacetate → HCID 56848966, compound

HRID 2407348Notes

Reaction equation

HRID 2407348 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1)[C:5]([O:7][CH3:8])=[O:6].[C:20](OCC)(OCC)(OCC)[CH3:21]>C(O)(=O)C>[CH3:20][C:21]1[N:12]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 61307110HCID 61307110, compound

Product 1

HCID 56848966HCID 56848966, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the compound obtained in Step 2 (0.46 g, 1.80 mmol) and triethyl orthoacetate (1.46 g, 9.00 mmol) was dissolved in 3 mL of acetic acid 3 mL, and stirred under reflux for 12 hours. The reacted mixture was cooled to room temperature and concentrated under reduced pressure, and then diluted with 20 mL of ethyl acetate. The resultant material was washed with 30 mL of a saturated aqueous solution of sodium carbonate twice and then 30 mL of water once, sequentially, and then the organic layer was taken, and dehydrated with anhydrous sodium sulfonate and concentrated under reduced pressure, and purified by a column chromatograph, to obtain methyl 2-methyl-1-m-tolyl-1H-benzo[d]imidazole-5-carboxylate as a purple solid (436 mg, 86%).

Workup

  1. temperatureunder reflux for 12 hours
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with 20 mL of ethyl acetate
  4. washThe resultant material was washed with 30 mL of a saturated aqueous solution of sodium carbonate twice
  5. concentrationconcentrated under reduced pressure
  6. custompurified by a column chromatograph

Sources & evidence

ORD record
ord-644597f01665480a87c77572fac90145
Source dataset
uspto-grants-2014_08
Patent number
US08809541B2

Reaction notes

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