Trimethyl orthoformate → HCID 68588564, compound

HRID 1496815Notes

Reaction equation

HRID 1496815 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][C:6]1[C:12]([CH3:13])=[CH:11][C:9]([NH2:10])=[C:8]([CH3:14])[CH:7]=1.[CH2:19]([NH:21][CH3:22])[CH3:20].[CH:23](OC)(OC)OC>>[CH2:19]([N:21]([CH3:23])[CH:22]=[N:10][C:9]1[CH:11]=[C:12]([CH3:13])[C:6]([O:5][C:4]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:2]([Cl:1])[CH:3]=2)=[CH:7][C:8]=1[CH3:14])[CH3:20]

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 68588616HCID 68588616, compound

Product 1

HCID 68588564HCID 68588564, compoundYield 80%

Procedure

200 mg (0.71 mmol) of 4-(3,4-dichlorophenoxy)-2,5-dimethylaniline are refluxed in 5 ml of trimethyl orthoformate for 4 h. The reaction mixture is cooled to room temperature and concentrated under reduced pressure on a rotary evaporator. The residue is taken up in 50 ml of dichloromethane and admixed with 84 mg (1.42 mmol) of N-ethyl-N-methylamine. After 16 h of stirring at room temperature, solvent and unreacted amine are removed under reduced pressure and the product is purified by column chromatography (230 mg, 88% purity, 80% yield, log P (pH 2.3)=2.48).

Workup

  1. concentrationconcentrated under reduced pressure on a rotary evaporator
  2. customsolvent and unreacted amine are removed under reduced pressure
  3. customthe product is purified by column chromatography (230 mg, 88% purity, 80% yield, log P (pH 2.3)=2.48)

Sources & evidence

ORD record
ord-d439c1b1d8f44d3b85187d541e414fd3
Source dataset
uspto-grants-2015_12
Patent number
US09199922B2

Reaction notes

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