Trimethyl orthoformate → HCID 25030825, compound

HRID 1919279Notes

Reaction equation

HRID 1919279 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([O:10][C:11]2[C:17]([CH3:18])=[CH:16][C:14]([NH2:15])=[C:13]([CH3:19])[CH:12]=2)[S:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([NH:22][CH3:23])[CH3:21].[CH:24](OC)(OC)OC>>[C:1]([C:5]1[N:9]=[C:8]([O:10][C:11]2[C:17]([CH3:18])=[CH:16][C:14]([N:15]=[CH:23][N:22]([CH2:20][CH3:21])[CH3:24])=[C:13]([CH3:19])[CH:12]=2)[S:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 44225694HCID 44225694, compound

Product 1

HCID 25030825HCID 25030825, compoundYield 59%

Procedure

17.46 g (63.00 mmol) of 4-[(3-(tert-butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylaniline are dissolved in 500 ml of trimethyl orthoformate and heated at reflux for 2 h. After cooling to ambient temperature (AT), the solvent is evaporated under vacuum and the residue is taken up in 630 ml of dichloromethane, treated with 8.65 ml (126.00 mmol) of N-ethyl-N-methylamine and stirred at ambient temperature for 18 h. After removing the solvent, the crude product is purified by column chromatography (13.4 g, 59% yield, 95% purity, log P (pH 2.3)=2.02).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. customthe solvent is evaporated under vacuum
  4. customAfter removing the solvent
  5. customthe crude product is purified by column chromatography (13.4 g, 59% yield, 95% purity, log P (pH 2.3)=2.02)

Sources & evidence

ORD record
ord-2e98640302d04eeaa03442f954ec607b
Source dataset
uspto-grants-2012_05
Patent number
US08168567B2

Reaction notes

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