N,N-Dimethylaniline → HCID 13691063, compound

HRID 2290732Notes

Reaction equation

HRID 2290732 reaction equation
[C:1](Cl)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]([CH3:31])[NH:26][C:27](=[O:30])[NH:28][N:29]=2)=[CH:20][CH:19]=1.CN(C)C1C=CC=CC=1>CN(C)C=O>[C:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:25]([CH3:31])[NH:26][C:27](=[O:30])[NH:28][N:29]=2)=[CH:22][CH:23]=1)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 66986Myristoyl chlorideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13691063HCID 13691063, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

With ice-cooling and stirring, a solution of tetradecanoyl chloride (2.83 g) in dimethylformamide (25 ml) was added dropwise to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.34 g) and N,N-dimethylaniline (1.53 g) in dimethylformamide (23 ml) over a period of 10 minutes. After completion of the addition, the mixture was stirred at room temperature for an additional 1.5 hours. The solvent was then distilled off under reduced pressure and 10% hydrochloric acid was added to the residue. The resulting crystalline powder was collected by filtration, washed with water and dried to give 6-(4-tetradecanoylaminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (3.82 g).

Workup

  1. temperatureWith ice-cooling
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred at room temperature for an additional 1.5 hours
  4. distillationThe solvent was then distilled off under reduced pressure and 10% hydrochloric acid
  5. additionwas added to the residue
  6. filtrationThe resulting crystalline powder was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-edf182b1c5a84076a007fbe2daab8356
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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