Triethylamine → HCID 21182419, compound

HRID 1386582Notes

Reaction equation

HRID 1386582 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[C:20](Cl)(=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C)C=O.C(OCC)(=O)C>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[N:12]=[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[NH:1][C:2]=2[CH:3]=1)=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66982Decanoyl chlorideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 21182419HCID 21182419, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of Methyl 3,4-diaminobenzoate (1.91 g) and triethylamine (0.56 g) in N,N-dimethylformamide (20 ml) was added decanoyl chloride (2.31 g), and the mixture was stirred for an hour at 0° C. The reaction mixture was diluted with ethyl acetate, and washed with water and brine. The separated organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (20 ml), and conc. sulfuric acid (0.05 ml) was added, and the mixture was stirred for 6 hours at 60° C. After cooling, the reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and washed with water and brine. The separated organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel eluted with (n-hexane:ethyl acetate=3:1) gave 5-Methoxycarbonyl-2-nonylbenzimidazole (1.40 g).

Workup

  1. washwashed with water and brine
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customfiltrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (20 ml)
  6. additionconc. sulfuric acid (0.05 ml) was added
  7. stirringthe mixture was stirred for 6 hours at 60° C
  8. temperatureAfter cooling
  9. customthe reaction mixture was evaporated under reduced pressure
  10. additionThe residue was diluted with ethyl acetate
  11. washwashed with water and brine
  12. dry with materialThe separated organic layer was dried over magnesium sulfate
  13. filtrationThe magnesium sulfate was filtered off
  14. customfiltrate was evaporated under reduced pressure
  15. customPurification of the residue by column chromatography on silica gel
  16. washeluted with (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-98f30c34b9974cee9bcb3c441f065335
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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