Dimethylformamide → Benzoic acid, 3-amino-4-chloro-, dodecyl ester

HRID 1415726Notes

Reaction equation

HRID 1415726 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 760923-Amino-4-chlorobenzoic acid

Product 1

HCID 11035192Benzoic acid, 3-amino-4-chloro-, dodecyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

17.2 g (0.1 mol) of 3-amino-4-chlorobenzoic 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. 27.4 g (0.11 mol) of dodecyl 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 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 32.3 g (yield 95%) of the desired product. Purity 99% or higher. Melting point 58.3-59.5° C. A result of the elemental analysis of this sample is 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 was separated
  7. concentrationconcentrated
  8. additiondiluted with 100 ml of methanol
  9. temperaturecooled
  10. customto precipitate crystals
  11. customThe crystals were separated by filtration
  12. customdried

Sources & evidence

ORD record
ord-f2db181b82ec489d95b7b133fbfc5472
Source dataset
uspto-grants-1999_06
Patent number
US05908955

Reaction notes

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