N-(dimethoxymethyl)-N-methylethanamine → HCID 44546592, compound

HRID 389828Notes

Reaction equation

HRID 389828 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][C:6]1[N:10]=[C:9]([O:11][C:12]2[C:18]([CH3:19])=[CH:17][C:15]([NH2:16])=[C:14]([CH3:20])[CH:13]=2)[S:8][N:7]=1.CO[CH:26](OC)[N:27]([CH2:29][CH3:30])[CH3:28]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][C:6]1[N:10]=[C:9]([O:11][C:12]2[C:18]([CH3:19])=[CH:17][C:15]([N:16]=[CH:26][N:27]([CH2:29][CH3:30])[CH3:28])=[C:14]([CH3:20])[CH:13]=2)[S:8][N:7]=1

Participants

4

Reactant 2

HCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 67080809HCID 67080809, compound

Product 1

HCID 44546592HCID 44546592, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.85 g (5.15 mmol) of 4-{[3-(3-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline are dissolved in 10 ml of toluene and treated with 1.37 g (10.31 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 12 h, subsequently cooled, freed of solvent under vacuum and purified by column chromatography. 0.59 g of product is obtained (99.0% purity, 27.3% yield; log P (pH2.3)=2.31).

Workup

  1. temperatureThe reaction mixture is refluxed for 12 h
  2. temperaturesubsequently cooled
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-488bfa76755140808b27e2978315145d
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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