Dimethylformamide → Tetradecyl 3-amino-4-methoxybenzoate

HRID 1415728Notes

Reaction equation

HRID 1415728 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 178233-Amino-4-methoxybenzoic acid

Product 1

HCID 22723855Tetradecyl 3-amino-4-methoxybenzoateYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

16.7 g (0.1 mol) of 3-amino-4-methoxybenzoic acid was added to 50 ml of N,N-dimethylformamide. Then 13.8 g (0.1 mol) of potassium carbonate was added to the solution obtained above, and the resulting mixture was stirred in the temperature range of from 20 to 30° C. for 30 min. 30.5 g (0.11 mol) of tetradecyl bromide was poured into the solution thus obtained, and the resulting solution was heated to 80° C., and allowed to react at the temperature for 1 hour. After completing the reaction, 50 ml of ethyl acetate, and 50 ml of water were added to the reaction mixture, and the organic layer obtained was separated, concentrated, diluted with 100 ml of methanol, and then cooled to precipitate crystals. The crystals were separated by filtration, and then dried to obtain 33.1 g (yield 91%) of the desired product. Purity 98% or higher. Melting point 54.0-56.0° C. A result of the elemental analysis of this sample was as follows:

Workup

  1. customobtained above, and the resulting mixture
  2. customthus obtained
  3. temperaturethe resulting solution was heated to 80° C.
  4. customto react at the temperature for 1 hour
  5. additionwere added to the reaction mixture
  6. customthe organic layer obtained
  7. customwas separated
  8. concentrationconcentrated
  9. additiondiluted with 100 ml of methanol
  10. temperaturecooled
  11. customto precipitate crystals
  12. customThe crystals were separated by filtration
  13. customdried

Sources & evidence

ORD record
ord-0b392b007e974cae8b945fb74dd97a1b
Source dataset
uspto-grants-1999_06
Patent number
US05908955

Reaction notes

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