Hydrochloric Acid → HCID 19876799, compound

HRID 1886040Notes

Reaction equation

HRID 1886040 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][CH2:12][CH2:13][NH:14]C(=O)C.Cl>CO>[NH2:14][CH2:13][CH2:12][NH:11][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19876826HCID 19876826, compound

Product 1

HCID 19876799HCID 19876799, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-[2-[(1-methyl-1H-benzimidazol-2-yl)amino]ethyl]acetamide (2.32 g, 9.98 mmol), 2N HCl (20 mL), and MeOH (20 mL) was heated under reflux for 20 hours. The mixture was concentrated, diluted with H2O, made basic (pH9) with 2.5N NaOH, and extracted with EtOAc. The combined extracts were dried and concentrated to give a brown oil. Purification by flash chromatography (eluent 10% MeOH/CH2Cl2) gave a yellow oil 1.47 g (77%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. concentrationThe mixture was concentrated
  4. additiondiluted with H2O
  5. extractionextracted with EtOAc
  6. customThe combined extracts were dried
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customPurification by flash chromatography (eluent 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7321103da4424e62b67272e0136ebb39
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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