Methanol → HCID 178428559, compound

HRID 2194334Notes

Reaction equation

HRID 2194334 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[S:14][N:13]=[C:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:11]=2)[C:6]([CH3:24])=[CH:5][C:3]=1[NH2:4].CO.O([CH:29](OC)[N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[S:14][N:13]=[C:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:11]=2)[C:6]([CH3:24])=[CH:5][C:3]=1/[N:4]=[CH:29]\[N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 887MethanolHCID 128853411-(Dimethoxymethyl)piperidineHCID 67238087HCID 67238087, compound

Product 1

HCID 178428559HCID 178428559, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.30 g (0.79 mmol) of 2-chloro-4-({3-[2-(4-chlorophenyl)ethyl]-1,2,4-thiadiazol-5-yl}oxy)-5-methylaniline is dissolved in 3 ml of toluene and 0.75 ml of methanol and treated with 0.37 g (2.37 mmol) of 1-(dimethoxylmethyl)piperidine. The reaction mixture is refluxed for 18 h, subsequently cooled, freed from the solvent under vacuum and purified by column chromatography. 0.13 g of product is obtained (84.2% purity, 29.3% yield, log P (pH 2.3)=2.64).

Workup

  1. temperatureThe reaction mixture is refluxed for 18 h
  2. temperaturesubsequently cooled
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-b06affc31664469c8473382281f58b3d
Source dataset
uspto-grants-2012_12
Patent number
US08334235B2

Reaction notes

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